Jockey Jim Culloty and Horse Best Mate after Cheltenham Gold Cup wins

The Cheltenham Gold Cup has ran for 200 years, as a steeplechase for almost 100 years of that history. It’s considered one of the most prestigious events in the Horse Racing calendar and takes place during the Cheltenham Festival each March. Cheltenham Gold Cup winners are among the most notable and recognisable jockeys, trainers and horses in all of horse racing. 

Ed Quigley dives down memory lane and highlights five races from yesteryear that created those goosebump moments at the home of National Hunt Racing…

Great Cheltenham Gold Cup wins this Century

Best Mate (2004)

Best Mate arrived at the 2004 Gold Cup on the cusp of racing history and immortality; looking to become the first horse since Arkle in 1966 to win three Gold Cups (in a row), there was a buzz of nervous excitement as the horses were called into line for the start of this one. That buzz gradually crescendoed into a feverish roar as the realisation of witnessing something special started to bear fruit; Jim Culloty and his willing friend were closing on the leaders coming down the hill towards the third last, but after jumping it cleanly, a momentary alarm bell went off amongst 70,000 people as he got hemmed in by the rail. Shuffling for racing room, Culloty had to bide his time and was forced to wait until he got into the home straight to angle his mount out for a challenge – just in time for the second last fence. The crowd sensed the gap was opening and the noise went up a notch once more; Best Mate pinged the second last to take the lead, aided in his pursuit by a wall of noise seldom heard in any sporting arena. He went on to win by half a length in one of the great Cheltenham Gold Cup wins in the history of the Cheltenham Festival.

Denman (2008)

There was a fantastic build-up to this one. Described by legendary scribe Alastair Down as “the most anticipated race in 44 years” it was a contest which captured the public’s imagination. Denman, a brute of a horse, affectionately known as ‘The Tank’ amongst his legions of followers, was undefeated as a chaser and a destructive winner of the RSA Chase12 months earlier. His more illustrious and aesthetically pleasing stablemate, Kauto Star was already a multiple Grade 1 winning superstar, and winner of the Gold Cup 12 months earlier. The Tank was sent off 9/4 second favourite, and after taking up the running on the second circuit, proceeded to gallop his rivals into the ground in a merciless display that lives long in the memory. Kauto Star was never really on his A-game – and perhaps he wasn’t able to be, such was the pressure he was under from a long way out; perhaps as a rarity, he was taken out of comfort zone. Sam Thomas and Denman galloped home by seven lengths, from a gritty, but punch-drunk Kauto Star, Neptune Collonges in third, making it a 1-2-3 for Paul Nicholls. The race, perfectly summarised at the end of commentator Richard Hoiles’ call: “Relentless, remorseless, he has pounded Kauto Star into submission…the answer is Denman!” He very much was the answer on that damp day in the shadow of Cleeve Hill, as anyone who witnessed it will never forget.

Kauto Star (2009)

Twelve months on, the tables were turned. Not all had been plain sailing with Denman after his 2008 heroics, as a heart issue resulted in him being off the track for 11 months. He came back at Kempton in February and was thumped 23 lengths by Madison Du Berlais. Kauto Star, on the other hand, arrived on the back of just mopping up his third King George. The result this time around was much more to the apparent script; on a hazy spring day, Kauto Star jumped and travelled with aplomb in the hands of Ruby Walsh – he had all his usual zest with him and he swaggered his way throughout the contest. One of the great racing photos is from the third last fence; Denman, Kauto Star and Neptune Collonges all jumping the obstacle in unison. King Kauto was on song and at his imperious best on this occasion, and when Walsh let out an inch of rein, the turbo was there. He majestically went through the gears to become the first horse to regain the Gold Cup, and did so by 13 lengths. Commentator, Simon Holt’s closing line of “Kauto Star canters home!” captured the ease and grace in which the talismanic star had made a big effort, seem totally effortless. 

Imperial Commander (2010)

Everyone knows a party pooper. Yet, no one was expecting any unwanted guests for the race billed as ‘Kauto v Denman – The Decider.’ The two great horses’ heads were on posters painted on the side of double-decker buses. London Underground tube stations had the rivals on billboards, and even World Champion Boxer David Haye got in on the act down at Paul Nicholls stable with a promotional afternoon likening each horse and their characteristics to of great pugilists of the present and past. Then there was Imperial Commander, the 7/1 shot who should have been 700/1 if the hype surrounding the two horses who had won the last three renewals was to be believed. Trainer Nigel Twiston-Davies rather sarcastically played the hype game on the Cheltenham Preview Night circuit, commenting “My lad has won five times at Cheltenham, but I suppose he has no chance!.” The race itself never really produced the final showdown between Kauto and Denman we wanted to see, as Kauto Star never jumped with any of his usual fluency, and after making a big error at the 8th fence, was always playing catch-up. It was a case of one too many mistakes from Kauto Star as he crashed out four from home, leaving old rival Denman in the lead – but with Paddy Brennan moving menacingly up on his outside with three fences to go. He went on to score by 7 lengths, and Brennan lapped up the moment by placing his finger to his lips in a big ‘Sshhh!’ sign to the packed galleries. There definitely was a party afterwards – just not the one many envisaged.

Coneygree (2015) 

“Was it a brave decision to run in the Gold Cup?” a question posed to Sara Bradstock, wife of the winning trainer Mark, in the immediate aftermath of victory. “Not really when you have a horse as brave as Coneygree!”. All connections were trying to hold back tears of sheer elation as Coneygree became the first novice since Captain Christy in 1974 to land the showpiece event at Prestbury Park. Coneygree was a fragile, but extremely talented beast who devoured his fences, and on that extremely wet day in 2015, jumped his rivals absolutely ragged on just his fourth chase start, justifying connections’ decision in no uncertain terms to not to go for the RSA Chase.

It had been a dry, sunny week in Cheltenham, but the rain arrived the night before and it hammered down turning this particular running of the Gold Cup into a proper war of attrition, conditions that jockey, Nico De Boinville, described as “Ideal for him.” It was quite a remarkable performance from the gelding who was rushed up in the hands of De Boinville to take the lead approaching the first fence – and didn’t see another rival. One by one, challengers cracked and wilted under the sustained and relentless gallop the eight-year-old set, and as he jumped the last victory looked to be in his sights. Just for a moment as they came up the Cheltenham Hill, there was a feeling Djakadam and Road To Riches were starting to reel in his inexperienced rival as Coneygree started to drift to the right. De Boinville galvanised his intrepid partner to land the spoils by one and a half lengths in a performance that was heartwarming and flawless in equal measure