With the Guineas Festival now in the rearview mirror, the Flat racing roadshow moves quickly on to Chester. There’ll be big hats, bold outfits, and barrels of prosecco, but there’s also the serious matter of some top-class racing.
My initial Chester May Festival betting tips involve events on Wednesday and Thursday, including in two crucial Derby trials.
Chester May Festival Tips: My 4 Best Bets
| Race | Horse | Odds | Bookmaker |
|---|---|---|---|
| 3:05 Wednesday | Water To Wine | 9/4 | bet365 |
| 3:40 Wednesday | Alaminos | 9/4 | StarSports |
| 2:35 Thursday | Morshdi | 11/4 | BetVictor |
| 3:05 Thursday | Rahiebb | 7/2 | Betway |
Odds correct at 15:00 BST on 05/05/26. Odds subject to change.
The Chester May Festival gets underway with two of the most informative days of the week. All eyes are on I’m The One in the Cheshire Oaks, who has been backed from 25/1 to 3/1 for the Oaks itself.
With value in mind, my Chester horse racing tips focus on the other key races across Wednesday and Thursday. I have four horses over the opening two days, narrowing in on the strongest angles.
I’ve taken into account the Chester draw bias statistics, which are crucial on this tight track, with my horses being priced up by bet365, BetVictor, Betway, and StarSports, some of the best bookmakers around.
Water To Wine (3:05 Wednesday) – No Miracles Required
This is the Chester Vase, the first of the crucial upcoming Derby trials. Aidan O’Brien, so often unstoppable at Chester, runs the new Derby favourite Benvenuto Cellini here, and his form does stack up. He has to give away 4lbs however, and that won’t be easy this time.
It’s well known just how strongly the John & Thady Gosden team have started this season. Their Kingman colt, Water To Wine, was outstanding on debut, and he looks tailor-made for this task.
He has been kept in the Derby at the latest forfeit stage, but it’s not yet clear whether the Epsom race, or the King Edward VII at Royal Ascot, will be his preferred target following this. Either way, he’s one of my Chester best bets.
Why I’m Backing Water To Wine:
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Showed real class on his debut
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Should suit the demands of Chester
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Heading to the top at some stage
Alaminos (3:40, Wednesday) – Sprinter Ready to Strike
In any six-furlong handicap at Chester, we need to be aware of two key things: pace and the draw. Alaminos (Kevin Ryan), is drawn just four off the rail, which is ideal, and definitely has the toe to be in the right position when it counts.
He was unlucky on his seasonal debut at Pontefract, where he got trapped and couldn’t get a run, but he’s improving all the time and can gain some compensation now. He is 9/4 with StarSports, who offer free bets as part of their new customer bonus.
Why I’m Backing Alaminos:
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An unlucky loser last time out
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Well handicapped and still lightly raced
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Drawn well and has the requisite pace
Morshdi (2:35, Thursday) – Haggas Hero on the Derby Trail
William Haggas’ Morshdi made such a good impression when he won the Feilden Stakes at the Craven Meeting three weeks ago. No sooner had he crossed the line, it was known that the Dee Stakes, another Derby prep, was next up for him.
Morshdi will have to take on another Aidan O’Brien hotpot in the shape of Constitution River, but as a late-maturing type, I’m backing him to improve past last season’s Curragh Group 2 winner.
The son of Dubawi, crucially out of a Galileo mare who brings stamina into the pedigree, is 25/1 for the Derby going into this week, but that will shrink heavily if he wins this.
Why I’m Backing Morshdi:
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Looked every inch a Derby type at Newmarket
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Will appreciate this extra furlong around Chester
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Drawn nicely for a top trainer who knows how to win here
Rahiebb (3:05, Thursday) – Cup Campaign Starts Here
In the same colours as Morshdi, those of Sheikh Ahmed al Maktoum, Rahiebb begins his four-year-old season for trainer Roger Varian, who is in strong form. An improver, this horse was placed at Group 2 level during Royal Ascot week, and then so very nearly ran down Aidan O’Brien’s winner in the St Leger.
He has been kept back since then, with a ‘Cup’ plan made for him. He is definitely a stayer, so should appreciate the Ormonde Stakes’ trip of nearly one and three-quarter miles. He is being lined up for a crack at the Ascot Gold Cup and the Goodwood Cup, among other things, and I reckon he can start the season off properly. He’s the last of my Chester horses racing tips for days one and two.
Why I’m Backing Rahiebb:
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Improving profile, went close at Group 1 level
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Trained as a ‘Cup’ horse this year
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Great value against two O’Brien horses
Why This Meeting Matters
Chester Racecourse, known as “The Roodee”, is picturesque and totally unique. The oldest course in Britain still in use, having been racing since 1539, this track presents horses with the task of handling tighter bends than they will encounter anywhere else.
The need for balance means trainers love to send potential Classic runners here to test them out. As such, the Dee Stakes and the Chester Vase, both legit trials for the Derby, and the Cheshire Oaks, great prep for the Oaks itself at Epsom, are key races on the calendar.
This is also a massive deal for the racegoers, with the May Festival being the main social event in Cheshire. With the TV cameras always present, everyone will be in their finery this week, especially on Ladies Day.
For me, it’s a great betting event and one of the reasons I love Flat racing. We don’t have to wait around for Saturday to come to get stuck into the top-class action.
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