• Home
  • Betting Tips

2021 Chester Cup Tips - Odds, trends and two horses to back

  • We've published our guide to the 2021 Chester Cup
  • This historic handicap headlines the card at Chester on Friday 7th May
  • Get the latest odds and some key trends right here
  • Not So Sleepy and Nate The Great are our two against the field
Not So Sleepy (left) hangs on for fourth after making the running in the 2020 Cesarewitch. (Getty)

Friday's card at Chester's May Festival is headlined by one of the biggest betting races of the year, the Chester Cup. This 18-furlong handicap was first staged on the Roudee way back in 1824, and a capacity field of 17 runners was confirmed ahead of the 2021 renewal.

We've taken a look at the odds and listed some key trends before picking our two against the field.

2021 Chester Cup Odds

Not So Sleepy6/1
Future Investment8/1
Falcon Eight9/1
Rare Groove10/1
Trumpet Man10/1
Who Dares Wins12/1

*Odds taken on 5/5/21*

2021 Chester Cup Trends

  • 13 of the last 15 winners went off at 16/1 or shorter (Only 1 winning favourite)
  • 13 of the last 15 winners had won a Class Two Handicap on the flat
  • 12 of the last 15 winners carried between 8-11 and 9-04
  • 12 of the last 15 winners were aged between 4 and 6
  • 11 of the last 15 winners had won over 2m
  • 11 of the last 15 winners were drawn in stall 11 or lower (68% of first three finishers in last 15 years were drawn 11 or lower)
  • 9 of the last 15 winners had run at least once that year
  • 9 of the last 15 winners were having their first run at Chester (4 of the other 6 had ran in the last Chester Cup)

2021 Chester Cup Tip 1 - Not So Sleepy

Not So Sleepy2021 Chester Cup TipsGET 6/1 HERE
18+ only. BetVictor is licensed and regulated as an online gaming operator in Great Britain, Ireland and Gibraltar. Gamble responsibly. Terms and Conditions apply.

Hughie Morrison's star shot straight to the head of the betting once the final field for this year's Chester Cup was confirmed. NOT SO SLEEPY isn't drawn particularly well in stall 13 and he's getting on a bit, but it's hard to knock his credentials.

Not So Sleepy has previous here at Chester, having won the Dee Stakes as a three-year-old back in 2015. In recent years, Morrison has campaigned his nine-year-old mainly over hurdles, and Not So Sleepy has enjoyed another strong National Hunt campaign, having won the Betfair Exchange Trophy at Ascot for the second year in a row, before a couple of solid runs in big Grade Ones at Cheltenham and Aintree.

Graham Lee was in the saddle when Not So Sleepy won over 12-furlongs at Pontefract in September, before running a cracking out in front to place fourth in the Cesarewitch. Not So Sleepy is now rated 100 on the flat and has 9-6 to carry, but I think he'll cope with it just fine.

nate the great
Nate The Great (left) winning a good staying handicap at Wolverhampton. (Getty)

2021 Chester Cup Tip 2 - Nate The Great

Nate The Great E/W2021 Chester Cup TipsGET 16/1 HERE
18+ only. Ts and Cs apply. Gamble responsibly. Coral is operated by LC International Limited and licensed and regulated by the British Gambling Commission for persons gambling in Great Britain. For persons gambling outside Great Britain, Coral is licensed by the Government of Gibraltar and regulated by the Gibraltar Gambling Commissioner.

I also fancy an each-way bet on NATE THE GREAT, for the in-form combination of Andrew Balding and David Probert.

After his form tailed off a little with Archie Watson, Nate The Great was moved to Balding's yard last summer. A strong fourth in the Queen Alexandra Stakes outlined his potential as a strong stayer, and Nate The Great went on to secure some excellent results during the all-weather season.

A runner-up finish behind the talented Australis was followed by a narrow third behind two very classy horses in Mildenberger and Rainbow Dreamer. Nate The Great then made the most of William Carver's claimer by beating Who Dares Wins and Lucky Deal in a handicap around Wolverhampton.

Nate The Great then looked a little outpaced on his return to turf racing at Musselburgh, staying on for fourth in the Queen's Cup. Themaxwecan, Cardano and Hochfeld finished ahead of Probert's mount that day, but Nate The Grate is much better off at the weights this time around, and he'll handle a little extra cut in the ground.


Not So Sleepy has proven form at the highest level on the flat and over jumps, and comes into this on the back of some strong performances over jumps.

Nate The Great remains a progressive stayer to follow, and both trainer and jockey are in excellent form.

2021 Chester Cup Tip 1: Not So Sleepy Straight Win @600.00 at BetMGM - 10 Units
2021 Chester Cup Tip 2: Nate The Great Each-Way @1500.0 at PlaySugarhouse Sport - 5 Units

Top Betting Sites

special-offer-1Special offers

Upcoming Events

16 October 2021

  • 2021 Queen Elizabeth II Challenge Cup
  • -
  • Horse Racing

17 October 2021

  • Sunday's Tips at Kempton and Naas
  • -
  • Horse Racing