The highlight race of the Cheltenham Festival is the £500,000 Betfred Cheltenham Gold Cup Chase (G1) for 5-year-olds and up. A field of 14 travelled the 3 5/16 miles over 22 fences, but the eyes of the racing world were on 12-year-old Kauto Star, sent off as the 3-1 second choice in his attempt to win his third Gold Cup. 12-1 Midnight Chase was sent to the lead early and he was pressed by Kauto Star and 7-4 favorite Long Run. After the 7th fence, Kauto Star faded badly and was eased by jockey Ruby Walsh. At the 18th fence, Midnight Chase tired, allowing 50-1 The Giant Bolster to inherit the lead. 8-1 Synchronised, last in the early stages, got to the front at the last jump to win by 2 1/4 lengths over The Giant Bolster in 6:36.20 over the good-to-soft course. It was another 3/4 length back to Long Run third.
Jonjo O'Neill, celebrating his first Gold Cup win as a trainer after winning twice as a jockey, said, "What a fantastic ride, he got him in a lovely jumping rhythm and it was just brilliant. Everyone has done so much with this fella at home, it's a team effort." Owner J.P. McManus, celebrating his first Gold Cup, said, "I've not had many runners but it's a pleasure to win it. I am so sorry Kauto Star pulled up but I gather he is OK and that's good news. It was lovely to win, he's not a Kauto Star but we've done it our way." Jockey Tony McCoy added, "It's great for Jonjo and J.P., he was off the bridle the whole way and he missed the third last but luckily he was close enough and he's an amazing horse. It's a brilliant training performance."
Paul Nicholls, trainer of Kauto Star said, "Ruby has done the right thing. There is obviously something tweaking him but he's fine." Owner Clive Smith added, "There will be no snap decision (on retirement) but I am 90% sure. I will take advice but someone will have to work very hard to persuade me that we should see him out again because what I wouldn't want to happen is have a Best Mate situation or a Dawn Run, I don't want anything like that, I'd just rather call it a day, maybe. We will see how we go and we will talk about it. It is a very sad occasion really because it will be the last time probably we will see him on the track. I feel a bit emotional now about it." Recognized as the greatest chaser since Arkle, Kauto Star has 2 Cheltenham Gold Cups, 5 King Georges, and 4 Betfair Chases among his 23 wins.