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Chepstow Racing Tips & Predictions - Friday 29th May 2026

Chepstow Racing Tips & Predictions - Friday 29th May 2026

Our Chepstow racing tips cover all 7 races on the card today, Friday 29th May 2026. The action gets underway at 14:00 and runs through to 17:10, with going reported as 7.4) (watering) (Good to firm, good in places (goingstick).

A few names jump off the page from a course-form perspective. Ajrad boasts a 42.86% strike rate from 7 runs at the track, Charlie Tucker has been in fine form here with 1 wins from 3 rides, Ralph Beckett’s yard sends out runners with a 29.79% strike rate at this venue. Below you’ll find race-by-race breakdowns with our top selections, live odds and tipster picks.

Tipster Performance at Chepstow

Here’s how the leading tipsters have fared at Chepstow over the last two years (minimum 10 selections):

TipsterSourceSelectionsWinsWin %Place %
MercuryDaily Post12650%91.67%
The Brigadierpunterslounge.com14642.86%78.57%
Jason HeaveyThe Star13430.77%84.62%
Mirror OnlineMirror Online10330%40%
Jim DelahuntScottish Sun10330%50%

14:00 – LSL Racing Horse Sales Syndication Leasing Apprentice Handicap

Race Details: 1m 4f | Class 6 | Going: 7.4) (watering) (Good to firm, good in places (goingstick) | | flat

This looks a fair little Class 6 rather than a complete minefield, though there are enough plausible angles to make it interesting. Oasis Sunrise brings the most solid recent profile to the table after a sequence of reliable efforts, while V Power arrives with winning form in the book and still looks competitive despite a small rise. Stage Show is respected after getting back on the scoresheet on return, but that came after an absence and this is a slightly deeper contest. Sea Of Charm and Trojan Truth are seasoned types who can get involved if the race is run to suit, while Endofastorm is weighted to be dangerous if reproducing his better placed efforts. Overall, consistency and tactical positioning should count for plenty over this trip.

Top Selections

1. Oasis Sunrise – 10/3 with Bet365

Jockey: Ashley Lewis | Trainer: Grace Harris | Form: -52132 | Rating: 72 | Topspeed: 55

Oasis Sunrise is the one I want on side because his recent form is simply the most dependable in the race. He has been knocking on the door in this sort of company, his figures reading like those of a horse holding his level well, and that Topspeed mark of 55 is right up there in this field. From stall 1, Ashley Lewis should be able to secure a handy position, and in a race lacking much mystery at the weights, that consistency becomes a major asset. At 10/3 with Bet365, he is not wildly overpriced, but he does look the runner with the fewest questions to answer. Bet: WIN

2. Endofastorm – 15/2 with Bet365

Jockey: Millie Wonnacott | Trainer: Joe Ponting | Form: 666225 | Rating: 73 | Topspeed: 50

Endofastorm makes some appeal as the each-way play because he has been running well enough in defeat and does not need to improve a stone to hit the frame again. Those back-to-back seconds stand out in the context of this race, and although he could only manage fifth last time, he remains on a workable mark and gets in here with just 121. In apprentice company, that sort of weight can be a real help late on over this trip. Millie Wonnacott knows how to deliver one from off the pace, and 15/2 with Bet365 feels a perfectly fair each-way price in an eight-runner field after the non-runner. Bet: EACH-WAY

Betting Strategy

Keep it straightforward: Oasis Sunrise is the win bet, as he brings the strongest recent profile and looks set for another big run. Endofastorm is the each-way option at a more tempting price, especially with his light weight and solid placed form. The obvious dangers are V Power, who remains in form, and Stage Show, whose comeback win gives him definite claims if backing that up.

Live Odds Comparison

HorseBet365BetfairPaddy PowerSky BetWilliam HillBest
Stage Show6/15/15/19/211/26/1 (Bet365)
Oasis Sunrise10/39/45/25/211/410/3 (Bet365)
Sea Of Charm5/19/25/15/15/15/1 (Bet365)
V Power7/211/211/211/24/111/2 (Betfair)
Trojan Truth5/14/19/29/25/15/1 (Bet365)
Sapphire Sirocco11/19/19/19/110/111/1 (Bet365)
Endofastorm15/26/113/213/27/115/2 (Bet365)
Paps Of Jura12/19/19/19/110/112/1 (Bet365)

14:30 – Finli Live Your Best Financial Life Handicap

Race Details: 1m 2f | Class 6 | Going: 7.4) (watering) (Good to firm, good in places (goingstick) | | flat

This doesn’t look the deepest 3yo handicap you’ll see at Chepstow, but it is a race with a fairly obvious shape. Regulus Black sets the standard on recent form and figures, arriving with the best official rating in the field and the strongest Topspeed number, so he’s no mystery at the head of the market. Behind him, Dash Of Class and Time To Sparkle have bits of handicap form that give them a squeak, while Gnocchi is a little harder to pin down but isn’t entirely dismissed. The rest need marked improvement or a sudden revival. In truth, this looks less a strong race than a winnable one for the right progressive type, and Regulus Black makes plenty of appeal if handling this track.

Top Selections

1. Regulus Black – 11/8 with Bet365

Jockey: Ross Coakley | Trainer: Hugo Palmer | Form: 4553 | Rating: 69 | Topspeed: 60

He’s the solid one in a race where solidity counts for plenty. Regulus Black has been knocking on the door in better order than most of these, and that latest third suggested this sort of Class 6 company is well within range. His mark of 69 is the highest in the field, his Topspeed of 60 is the standout figure, and there’s no great leap of faith required to see him taking another step forward over 1m2f. Hugo Palmer’s runner looks to have the right profile for this grade, and while 11/8 is no giveaway, he’s hard to oppose against rivals who have more to prove. Bet: WIN

Bet: WIN

2. Time To Sparkle – 9/2 with Bet365

Jockey: Jonny Peate | Trainer: James Keane | Form: -49153 | Rating: 65 | Topspeed: 59

Time To Sparkle makes plenty of each-way appeal in a race lacking depth beyond the favourite. She has at least shown she can be competitive in handicaps, winning before backing that up with respectable placed efforts, and her Topspeed figure of 59 says she’s not far off the favourite on raw numbers. The recent sequence reads well enough for this level and she doesn’t look exposed as a 3yo over this trip. At 9/2, she’s not wildly overlooked, but she does look the value alternative if Regulus Black underperforms or finds one too good late on. In an eight-runner field, she’s a sensible each-way punt. Bet: EACH-WAY

Bet: EACH-WAY

Betting Strategy

Keep it straightforward here. Regulus Black is the win play because he brings the best recent form, the best rating and the strongest speed figure into a modest race. Time To Sparkle is the each-way alternative, with enough consistency and a solid profile to make the frame. Dash Of Class is the obvious danger if building on recent handicap efforts.

Live Odds Comparison

HorseBet365BetfairPaddy PowerSky BetWilliam HillBest
Gnocchi7/115/217/28/16/117/2 (Paddy Power)
Time To Sparkle9/29/29/29/29/29/2 (Bet365)
Echo Valley33/125/125/125/128/133/1 (Bet365)
Dash Of Class7/216/516/53/17/27/2 (Bet365)
Regulus Black11/811/1011/1011/105/411/8 (Bet365)
Go For Gold10/112/114/114/112/114/1 (Paddy Power)
Leia Antilles18/116/118/118/118/118/1 (Bet365)
No Drama Mama12/117/210/19/111/112/1 (Bet365)

15:00 – Bill Lewtons 80th Birthday Novice Stakes

Race Details: 1m 2f | Class 3 | Going: 7.4) (watering) (Good to firm, good in places (goingstick) | | flat

This does not look the deepest novice you will ever see and, on paper at least, it revolves around the three-year-olds with established form. Alfaraz sets the standard on a mark of 93 and is the obvious one after keeping better company, while Echo Of Stars and El Nay bring solid enough placed form to the table and should make him work for it. The older horses look badly up against it, with Strong Man Tom and Prophet Squeeze huge prices for good reason, while debutant Kinetic Impact adds a bit of intrigue without bringing any hard evidence. Over this sharp enough 1m2f on quick ground, tactical speed and a bit of professionalism are likely to matter. It is not an impossible puzzle, but the market leaders do look to have this between them.

Top Selections

1. Alfaraz – 4/5 with Bet365

Jockey: David Probert | Trainer: Andrew Balding | Form: 22-6 | Rating: 93 | Topspeed: 86

Alfaraz is hard to oppose on the bare numbers. A mark of 93 sets a clear standard in this field and his earlier placed efforts already read well enough for a race of this nature. The slight concern is that he was only sixth on his return, but Balding’s three-year-olds often sharpen up for a run and this looks a much more manageable assignment. David Probert is a positive booking and, from stall 2, he should be able to secure a handy position without fuss. At around 4/5 he is not exactly hidden from the market, but this is the likeliest winner and the one they all have to beat. Bet: WIN

2. Echo Of Stars – 7/2 with William Hill

Jockey: Jamie Spencer | Trainer: Oliver Cole | Form: 42-4 | Rating: 89 | Topspeed: 79

Echo Of Stars appeals as the each-way play because he has already shown a fair level of ability and does not need to improve dramatically to hit the frame again. His rating of 89 puts him second on official figures, and that latest fourth after a break suggested there should be a bit more to come now stepping up in trip again. Jamie Spencer is the sort you want if this turns tactical and they crawl before quickening, and stall 1 gives him options. At 7/2 he is not wildly overpriced, but in an eight-runner race with three places on offer he makes plenty of sense as the solid each-way alternative to the favourite. Bet: EACH-WAY

Betting Strategy

Keep it simple. Alfaraz is the win bet because he brings the best form and the highest rating into a race lacking depth. For an each-way punt, Echo Of Stars looks the sensible play given his proven level and likelihood of progressing from his return. El Nay is the obvious danger if building on his consistent profile, while Kinetic Impact is the unknown quantity.

Live Odds Comparison

HorseBet365BetfairPaddy PowerSky BetWilliam HillBest
Strong Man Tom200/1150/1150/1150/1150/1200/1 (Bet365)
Madame Dragon80/166/166/166/166/180/1 (Bet365)
Prophet Squeeze125/1100/1100/1100/1100/1125/1 (Bet365)
Alfaraz4/54/64/64/64/54/5 (Bet365)
Blue Hercules9/115/217/27/117/29/1 (Bet365)
Echo Of Stars10/316/510/310/37/27/2 (William Hill)
El Nay4/118/54/17/27/24/1 (Bet365)
Kinetic Impact14/110/112/110/112/114/1 (Bet365)

Tipster Selections

TipsterSelection
The JudgeAlfaraz
Jeffrey RossEcho Of Stars

15:30 – 3 Day Pass £30 DragonBet WRF Handicap

Race Details: 5f | Class 5 | Going: 7.4) (watering) (Good to firm, good in places (goingstick) | | flat

This may only be a five-runner sprint, but it is not lacking in angles. Cayman Tai arrives on the back of a deserved win and is the obvious one after a solid sequence, while On Edge and In The City both bring consistent handicap form to the table without looking bombproof finishers. Over Spiced is a bit harder to weigh up, having mixed a win with a couple of lesser efforts since, and So Smart is the lightweight lurking on the rail if this turns tactical. In a race of this size, track position and early sharpness over 5f will matter plenty, and there is a fair chance the market gets this right. Even so, it is not an especially deep Class 5 and one runner does look to hold the clearest claims.

Top Selections

1. Cayman Tai – 5/4 with Bet365

Jockey: Seamus Cronin | Trainer: Richard Hannon | Form: 525321 | Rating: 84 | Topspeed: 64

Cayman Tai is hard to oppose in a race lacking much mystery but not much depth either. He has been knocking on the door for a while, his recent form figures reading well in the context of this small-field handicap, and he finally got his head in front last time. An opening mark of 84 does not look harsh given how steadily he has been progressing, and the Hannon yard is well used to placing this type to good effect. He does not set an intimidating Topspeed figure, but this looks more about reliability and race shape than raw numbers. At 5/4 he is no giveaway, but he is the solid one.

Bet: WIN

Betting Strategy

Keep it simple in a five-runner race: Cayman Tai is the win bet and the only play. Each-way betting has little appeal with just two places on offer, and the obvious dangers are On Edge for his proven consistency and In The City if he can build on his latest run. But the percentage call is to side with the favourite.

Live Odds Comparison

HorseBet365BetfairPaddy PowerSky BetWilliam HillBest
On Edge11/211/26/16/16/16/1 (Paddy Power)
Cayman Tai5/411/1011/1011/106/55/4 (Bet365)
In The City13/25/15/19/211/213/2 (Bet365)
Over Spiced4/14/14/14/14/14/1 (Bet365)
So Smart4/14/19/29/29/29/2 (Paddy Power)

Tipster Selections

TipsterSelection
Luke TuckerCayman Tai
The Data DetectiveCayman Tai
LambournIn The City

16:05 – UB40 Live After Racing 24th July Handicap (Chepstow Mile Series Qualifier)

Race Details: 1m | Class 6 | Going: 7.4) (watering) (Good to firm, good in places (goingstick) | | flat

This is not a deep Class 6 by any means and the market has latched on to the obvious one in Thanos, who arrives off the back of a breakthrough win and now looks well placed to follow up despite top weight. He sets the standard on recent form and is very much the horse they all have to beat. The interesting angle is whether anything can make it awkward for him in a small field, and Alice’s Influence looks the most likely after a solid 1-2 sequence in handicaps. Mooj is entitled to step forward from a quiet reappearance, but the rest have a fair bit to prove on what they have shown so far. In truth, this looks more straightforward than fiendish, with the favourite holding strong claims.

Top Selections

1. Thanos – 8/11 with Bet365

Jockey: Lewis Edmunds | Trainer: Harry Charlton | Form: 922-21 | Rating: 70 | Topspeed: 55

Thanos is hard to oppose in a race of this quality. He had been knocking on the door last season, returned with another solid run when second, and then did what was required to get off the mark last time. That form line is easily the most persuasive piece on offer here and an opening mark of 70 still looks workable in this company. Harry Charlton’s 3yo is drawn widest in seven, but in a race lacking depth that should not be enough to put you off. At 8/11 he is no giveaway, but he is the most progressive sort in the line-up and the one with the clearest upside. Bet: WIN

Bet: WIN

2. Alice’s Influence

Jockey: David Probert | Trainer: David Evans | Form: 59-412 | Rating: 67 | Topspeed: 54

Alice’s Influence makes more each-way appeal than most in a race where several arrive with little momentum. She has plainly improved since being sent into handicaps, winning before backing that up with a close second, and that gives her a solid platform here from a low draw in stall one. David Probert is a positive booking for a filly who looks uncomplicated and should get a handy trip around this sharp mile. She may not have quite the same scope as Thanos, but she is reliable at this level and looks the likeliest to chase him home if he runs to form. Bet: EACH-WAY

Bet: EACH-WAY

Betting Strategy

Keep it simple. Thanos is the win play because he brings the strongest recent form and still looks ahead of his mark in a weak Class 6. For those wanting a bit of insurance in a seven-runner race with three places on offer, Alice’s Influence is the sensible each-way punt. Mooj is the obvious danger if bouncing back, but he has more to prove right now.

Live Odds Comparison

HorseBet365BetfairPaddy PowerSky BetWilliam HillBest
Thanos8/118/118/118/118/118/11 (Bet365)
Lihou Lady18/116/118/118/118/118/1 (Bet365)
Mooj9/218/54/14/14/19/2 (Bet365)
Violet Goldsmith14/111/112/111/112/114/1 (Bet365)
Diamond Aura28/125/125/125/122/128/1 (Bet365)
Karmacy40/133/133/133/133/140/1 (Bet365)

Tipster Selections

TipsterSelection
MoorestyleThanos
The GuardianThanos

16:40 – LSL Racing Horse Sales Syndication Leasing Maiden Stakes

Race Details: 7f | Class 4 | Going: 7.4) (watering) (Good to firm, good in places (goingstick) | | flat

This looks a fairly informative little maiden rather than a numbers game, with the market understandably revolving around Food For Thought after a useful two-run juvenile campaign. He sets the standard on a mark of 92 and if he has trained on, the rest may be playing for places. That said, it is not a one-horse race. Quisana shaped with promise on debut, Guitar Solo has shown enough to think a 7f maiden can be within reach, and newcomer Ingemar comes from a yard capable of readying one first time. A couple of the bigger prices, notably Diane Chasseresse, are not without interest either. Still, this is the sort of race where proven ability usually counts for plenty, and the Beckett runner is hard to oppose.

Top Selections

1. Food For Thought – 10/11 with Bet365

Jockey: Rossa Ryan | Trainer: Ralph Beckett | Form: 62- | Rating: 92 | Topspeed: 59

He is the obvious one, but not for flimsy reasons. A mark of 92 stands out in this field and his two runs last season suggest he was learning quickly, finishing sixth before stepping forward to be second. Beckett does very well with this type of patiently handled three-year-old, and Rossa Ryan is exactly the sort you want aboard in a race where tactical positioning over 7f could matter. Odds of 10/11 are not flashy, but they are fair enough if you believe normal improvement from two to three is coming. In a race lacking depth, he holds the strongest claims and looks the solid win play.

Bet: WIN

2. Quisana – 4/1 with Bet365

Jockey: Charles Bishop | Trainer: Eve Johnson Houghton | Form: 4 | Rating: 88 | Topspeed: 66

For an each-way angle, Quisana makes more appeal than the more exposed alternatives. She was fourth on debut, which does not scream headline performance, but an opening mark of 88 tells you she showed a fair bit more than the bare form might suggest. The Topspeed figure of 66 is also perfectly respectable in the context of this race, and natural improvement from first to second start would put her firmly in the mix. At around 4/1 she is not a huge price, but in a seven-runner race with only two places she still looks the most credible one to chase the favourite home. She is the sensible each-way punt.

Bet: EACH-WAY

Betting Strategy

Keep it straightforward: Food For Thought is the win bet because he brings the best form, the best rating and the strongest stable profile. For those wanting a saver or place-focused play, Quisana is the each-way option as the most likely improver among the challengers. Guitar Solo and debutant Ingemar are the obvious dangers if the favourite underperforms.

Live Odds Comparison

HorseBet365BetfairPaddy PowerSky BetWilliam HillBest
Brocklesby Bill50/133/133/133/140/150/1 (Bet365)
Ingemar6/111/26/15/16/16/1 (Bet365)
Watercraft22/120/122/120/120/122/1 (Bet365)
Diane Chasseresse22/118/120/118/120/122/1 (Bet365)
Food For Thought10/114/54/54/510/1110/11 (Bet365)
Guitar Solo4/17/24/17/24/14/1 (Bet365)
Quisana4/110/37/27/24/14/1 (Bet365)

Tipster Selections

TipsterSelection
West CountryBrocklesby Bill
MercuryFood For Thought

17:10 – DragonBet Welsh Racing Festival 9-11th October Handicap

Race Details: 7f | Class 6 | Going: 7.4) (watering) (Good to firm, good in places (goingstick) | | flat

This is a proper end-of-card handicap, competitive without being especially deep, and there are several with bits of exposed Class 6 form that tie in closely. Romanovich brings the most solid recent profile after winning earlier in the spring and again running respectably last time, while Too Much Trevor is lurking on a dangerous mark at the foot of the weights after a better effort on his latest start. Connie’s Rose has been knocking on the door and is clearly respected, and King Of The Dance is another who keeps threatening to get his head back in front. The pace and draw could matter over this 7f, but in truth this looks the sort of race where current sharpness and handicapping edge will decide it rather than raw talent. Tricky enough, but not impossible.

Top Selections

1. Romanovich – 4/1 with Bet365

Jockey: Ashley Lewis | Trainer: John O’Shea | Form: 951635 | Rating: 81 | Topspeed: 64

Romanovich makes plenty of appeal in a race where a lot of these are either thoroughly exposed or arrive with questions to answer. He won off this sort of mark not long ago and his latest fifth was perfectly respectable in the context of this grade, suggesting he is still in form and still capable of making his presence felt. Stall 2 looks workable, and John O’Shea’s runner has the profile of one who should get a handy position and keep finding. At 4/1 he is hardly a hidden gem, but he is the one with the fewest negatives and that counts for plenty in this company. Bet: WIN

Bet: WIN

2. Too Much Trevor – 11/2 with Bet365

Jockey: Olivia Tubb | Trainer: Grace Harris | Form: 446-52 | Rating: 80 | Topspeed: 71

Too Much Trevor looks the each-way play because he is very well treated on the figures and comes here after shaping as though a return to form is near. That latest second was a good step back in the right direction, and the standout feature is the low racing weight of 116, which gives him a major chance if he can build on that run again. Grace Harris also saddles Connie’s Rose, but this one may be the better value of the pair at around 11/2, especially with three places on offer in a 10-runner race. He does not need to improve much to go very close from this mark. Bet: EACH-WAY

Bet: EACH-WAY

Betting Strategy

Romanovich is the straight win bet because he brings the most convincing recent form into an ordinary Class 6. Too Much Trevor is the each-way option, with his feather weight and latest second making him very easy to like for place purposes and more. Connie’s Rose is the obvious danger, while King Of The Dance is another to keep onside in multiples after a string of solid efforts.

Live Odds Comparison

HorseBet365BetfairPaddy PowerSky BetWilliam HillBest
Redredrobin14/114/114/111/114/114/1 (Bet365)
Forever My Prince15/211/213/211/27/115/2 (Bet365)
Northcliff14/116/116/112/114/116/1 (Betfair)
Vape9/110/111/110/110/111/1 (Paddy Power)
Ajrad11/29/25/14/15/111/2 (Bet365)
Romanovich4/14/14/14/14/14/1 (Bet365)
King Of The Dance5/19/25/19/25/15/1 (Bet365)
Oviedo25/128/118/122/118/128/1 (Betfair)
Too Much Trevor11/29/25/19/25/111/2 (Bet365)

Tipster Selections

TipsterSelection
On The NoseConnie’s Rose
WhistlerConnie’s Rose
The PuntRedredrobin
RP RatingsRomanovich

Chepstow Course Specialists

Horses To Note

The top course performers among today’s runners:

HorseRunsWinsWin %Place %
Ajrad7342.86%85.71%
On Edge8337.5%62.5%
Trojan Truth3133.33%33.33%
Romanovich13430.77%38.46%
Redredrobin10330%70%

Jockeys To Note

The pilots with the strongest records at the course:

JockeyRidesWinsWin %Place %
Charlie Tucker3133.33%66.67%
Rossa Ryan1883820.21%43.62%
Ross Coakley48816.67%41.67%
Gina Mangan1792715.08%32.4%
Millie Wonnacott20315%40%

Trainers To Note

Yards that have done well at Chepstow:

TrainerRunnersWinsWin %Place %
Ralph Beckett471429.79%51.06%
Hugo Palmer22627.27%45.45%
William Muir & Chris Grassick18422.22%38.89%
Andrew Balding601321.67%43.33%
Dr Richard Newland & Jamie Insole19421.05%63.16%

Summary & Best Bets

That wraps up our Chepstow racing tips for Friday 29th May 2026. We’ve covered all 7 races with our top selections highlighted above. Use the betting strategies as a starting point, always shop around for the best odds, and never bet more than you can afford to lose.

FAQ

What time does racing start at Chepstow today?

The first race at Chepstow on Friday 29th May 2026 goes off at 14:00, with 7 races scheduled in total.

What is the going at Chepstow today?

The going at Chepstow is reported as 7.4) (watering) (Good to firm, good in places (goingstick).

How many races are at Chepstow today?

There are 7 races on the card at Chepstow today, running from 14:00 through to 17:10.

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