Cheltenham Festival: Greatest Rides

The Cheltenham Festival is the greatest four days of jumps racing on the calendar and here we cast our minds back through the years and look at some of the greatest rides from the showpiece meeting in the Cotswolds.

Having the right horse for winning a race at Cheltenham is key but, sometimes, things don't go to plan on the big day and, in those moments, talent and judgement in the saddle can make all the difference.

Follow every moment from the 2024 Cheltenham Festival via the bet365 Sports Live Streaming platform and check out our guide to some of the horses and trainers to follow at the biggest jumps festival of them all. 

Denman pounds Kauto Star into submission

Denman - 2008 Gold Cup

Denman and Kauto Star were more like rock stars than staying chasers in the build-up to the Cheltenham Gold Cup in 2008. They were both trained by Paul Nicholls and lived side-by-side in his Ditcheat yard.

They were top-class and the Gold Cup had long been established as the place they'd meet for the first time competitively. Their story captivated a wider sporting audience and they made front page news in the national media as the race loomed up.

Kauto Star, the defending champion, was favourite but it was Denman who reigned supreme on this particular day.

Sam Thomas, on Denman after Ruby Walsh elected to stick with Kauto Star, deserves huge praise for his courageous attacking ride.

With a full circuit of Prestbury Park still to run, he sent Denman to the front and they attacked from that point on. Kauto was in trouble some way from home and the winner held a 10-length lead entering the home straight.

Though Denman tired late on, he'd done enough to blunt the finishing power of his rival. As commentator Richard Hoiles famously remarked Denman and Thomas on that day were "relentless, remorseless" and had "pounded Kauto Star into submission".

Nicholls hasn't won a Gold Cup since King Kauto regained his crown in 2009, with the Ditcheat supremo seeing his King George winner Bravemansgame finish second to Galopin Des Champs in 2023.

McCoy carries Wichita Lineman home

Wichita Lineman - 2009 Festival Trophy Handicap Chase

AP McCoy was, for a generation of race fans quite simply, 'The Champ'. He was Britain's champion jockey for two decades, every single year that he was a professional, in a sporting feat that is unlikely to be matched.

McCoy was known for putting the same effort into Worcester on a summer's evening as he did this amphitheatre at Cheltenham in spring. Every time he was legged up on a horse, he had an insatiable desire to win - no matter the occasion or lack thereof.

He rode 31 Cheltenham Festival winners in his career and the one that is recalled most fondly is still Wichita Lineman in 2009.

In a competitive handicap, Wichita Lineman began to make mistakes from the ninth fence, and came off the bridle with a circuit to go as he dropped towards the rear. His chance looked forlorn as McCoy's urgings became more animated throughout that final circuit.

A shoddy jump at three-out might have done for most jockeys, but McCoy wasn't about to give in and Wichita Lineman closed in on the home straight, although jumping the last Maljimar was a good four-lengths clear and the voice of commentator Mike Cattermole suggested it was a done deal.

McCoy had other ideas and his partner duly surged home, hitting the front inside the final 50-yards on the 5/1 favourite, much to the delight of the packed Cheltenham grandstands.

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Lord Windermere - 2014 Gold Cup

If ever there was a race to define a rider it was Lord Windermere's Gold Cup win in the hands of the Davy Russell in 2014.

The Irish jockey rode a winner at every Cheltenham Festival from 2006-2018 and is regarded as one of the finest horsemen of his generation. On this day, he needed every ounce of nous and persuasion to steer home a partner that seemingly lacked an interest in the job at hand.

Trained by Jim Culloty - rider of three-time Gold Cup winner Best Mate - Lord Windermere was no star and arrived to the Cotswolds having been beaten a combined 37-lengths in the Lexus Chase and Irish Gold Cup on his previous two starts.

He'd won the three-mile novice chase at the Cheltenham Festival a year earlier and so connections were hopeful returning to the Cotswolds would ignite his desire again.

It didn't quite go like that on the day. Russell's mount was in rear, or sometimes completely out the back in the race and didn't seem all that keen. His partner hunted him around, kept him interested and prepared him for one major push at the business end.

Before the second last, that moment came and Lord Windermere responded to Russell's urgings. They got to the front but On His Own and The Giant Bolster were frantically trying to overhaul them. A short-head split the first and second on the line, the slenderest winning margin in the Gold Cup since Cool Ground denied The Fellow in 1992.

Lord Windermere never won again over fences and was just 3-22 in this discipline in his career, an enigmatic but talented sort, his biggest win owed much to the powers of persuasion from the man on his back.

Ruby continues to make Big Buck's pay

Big Buck's - Stayers' Hurdle 2012

He's the all-time leading rider at the Cheltenham Festival with 59 and, while many of Ruby Walsh's wins came in sheer style, there were plenty that needed some working out too.

Big Buck's won the Stayers' Hurdle four times on the trot from 2009 onwards and Walsh's partnership with him on the turf at Cheltenham brought seven wins in seven starts together.

Their last Cheltenham outing, the 2012 Stayers' Hurdle, was a true feat of guile in the saddle.

Big Buck's had the lead at two out but the pretenders to his crown were hot on his heels and he was notoriously a horse that could do the minimum in front.

As they ran to the final flight, the mare Voler La Vedette was travelling noticeably well in the middle of the track, away from the leader.

Walsh, eager to keep the mind of Big Buck's on the job, crossed over to join her, but Andrew Lynch was having none of that, the pair criss-crossing as Big Buck's was momentarily on his own in the middle as the mare grabbed the running rail.

Coming up the hill, Walsh again moved Big Buck's inwards, eye-balling his prey and knowing that in doing so, the champion would stare her down and see off the challenge.

That he did, for an incredible 16th consecutive race win and an unprecedented fourth Stayers' crown, only seeing off the gallant mare inside the final 50 yards.

Townend's masterclass on Galopin Des Champs

Galopin Des Champs – Gold Cup 2023

It's quite something when Sir Anthony McCoy describes a Gold Cup performance as being 'as brilliant a ride as I've ever seen in any horse race' but that is what the 20-time champion jockey had to say in the aftermath of Paul Townend's win on Galopin Des Champs. 

The favourite was caught further back than ideal and didn't always jump with the fluency that had characterised his season to date, but Townend was ice-cool on board and rode a patient race.

He brought the market leader onto the heels of the leaders after the third last and, demonstrating his calmness, was seen to take a pull before two out as he played a classy waiting game. 

Once unleased, Galopin Des Champs joined King George winner Bravemansgame and they jumped the last in unison before Townend and his partner accelerated clear to win in style. 

It was Townend's third Gold Cup in five years and Galopin Des Champs is priced at 4/6 to repeat the win in 2024.

Elaborating on ITV Racing, McCoy added: "Talk about the pressure, talk about riding a horse with bottle. He coped with it better than anyone I've ever seen.

"He was so cool, riding such a fancied horse, at the Cheltenham festival, in the Cheltenham Gold Cup. So cool...And he delivered." 

High praise indeed for a rider seemingly never more at ease than when the pressure it at its utmost.