Horse racing expert Will Smith has added this 1-star * 25/1 EW ante-post tip from Doncaster's Friday meeting.
Friday 23rd October 15:35
Horse racing analyst Will Smith returns to the jumps ante-post scene with this 2-star ** 5/1 EW pick for Cheltenham on Friday.
Home » Betting Tips » Horse Racing » squareintheair.com Handicap Chase – Cheltenham 3.35 – Friday 23rd October
| Bookie | Selection | Best Odds | Market | Bet |
|---|---|---|---|---|
![]() |
Calico | 5/15/1 | Ante Post
** EW 3 places 1/4 Cheltenham 3.35 - Fri 23 Oct |
Place BetPlace Bet |
Date of Tips: 19/10/2026
Disclaimer The odds for these selections were correct at the time of publishing (10:31 19/10/2026) but may have changed since. Please check the latest price before placing your bet.
There’s absolutely no stopping the Skelton juggernaut at the moment, as Dan remains firmly on track to break Martin Pipe’s all-time seasonal winners record, and in doing so will likely ensure he regains the trainer’s title once again.
Once again, it is a mix of careful planning and what appears to be a meticulous path plotted for every single horse, whether it be summer jumpers acquired to rack up sequences, or classy winter horses who are pinpointed at a certain race (or two).
There’s complete certainty that Friday’s squareintheair.com Handicap Chase at 3.35 at Cheltenham is Calico’s ‘Gold Cup’ for the season. That it comes on his first start of the season is no surprise, as he has won this race fresh in each of the last two seasons. He will be trained to the minute and won’t just be 99.9% fit, he will be 100% ready.
At 5/1 each-way with Bet365 or William Hill, and with just enough availability elsewhere at 7/2+ to make this recommendation worthwhile, he is a 2-star ** ante-post pick for WhichBookie. He will surely be a 7/4 shot on the day.
There is a fairly wet forecast for the week down in the Cotswolds, and while better ground would be ideal, Calico won this race last year on ‘good to soft’ and was a very creditable 4th in the Game Spirit on heavy ground behind Lulamba in February.
What matters more is that he will be fit enough to finish off his race if the ground gets testing, whereas the likely opposition will be a mix of horses only just starting out and summer ‘fast’ ground lovers.
If there were to be dangers, both Brookie and Boothill have got themselves extremely well-handicapped but will be very much on the retrieval trail against a hard-fit and potent Calico.
October 19, 2026 - Will Smith
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What's New?
Horse racing expert Will Smith has added this 1-star * 25/1 EW ante-post tip from Doncaster's Friday meeting.
Horse racing analyst Will Smith returns to the jumps ante-post scene with this 2-star ** 5/1 EW pick for Cheltenham on Friday.
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