Stradivarius, 2018, 2019 & 2020
What better way to start the list than the most recent prolific winner, Stradivarius, who won the race three times in succession between 2018 and 2020 for trainer John Gosden when partnered by Frankie Dettori in all of those wins.
He won one of his three starts as a two-year-old before emerging as a potential high-class stayer the following year, winning three times and placing three times from six starts, including when successful in the Queen’s Vase at Royal Ascot and the Goodwood Cup.
His first Ascot Gold Cup start came in 2018, which saw him sent off 7/4 and he defeated one of France’s smart stayers in Vazirabad by three quarters of a length in what was a thrilling finish to the contest.
This success led to him going on a 10-race winning sequence between May 2018 and September 2019, in which he claimed most of the best staying events the UK had to offer.
In this time, he added another Gold Cup success the following year, where he beat Dee Ex Bee by a length before his winning come came to an end by the smallest of margins, when a short-head second to Kew Gardens in the British Champions Long Distance Cup.
He was then third on his reappearance at Newmarket before landing a memorable third Gold Cup in 2020 when sent off evens favourite, winning the race by 10 lengths and cementing himself into the history books as a result.
He ran in two more Gold Cup’s in 2021 and 2022, respectively finishing fourth and third and concluded his career with an agonising neck second to Kyprios in the Goodwood Cup, which was undoubtedly one of the races of the season.
In total, he ran 35 times, winning 20 of those and amounted more than £3.5 million in prize earnings. His third and final win in the Gold Cup was one of the most impressive performances in the history of the race.
In my opinion, he is the GOAT of the stayers division and his longevity was remarkably outstanding. I don’t think we will see another quite like him and with everything taking into account, it was a no-brainer in regards to him being one of my favourite winners of this race and he did it three times.
Big Orange, 2017
A real fan favourite was Big Orange, who will be remembered for his tough and genuine attitude and showcased that by winning this race six years ago in what was one of the best finishes to the race in the history of the contest.
He was always towards the front under James Doyle and he appeared to beat off all the field but Ryan Moore galvanised Order Of St George to lay down a serious challenge.
While it looked for all the world as though Micheal Bell’s charge was going to be beaten, he bravely rallied to get his nose in front where it mattered.
It was a brave as performance as you’ll see in a staying event and was definitely one of my favourite ever winners of the race, plus I was lucky enough to have witnessed his greatest achievement in the flesh.
He also won a pair of Goodwood Cup’s in his time and a few other high-profile wins alongside placing in a Melbourne Cup. He had the heart of a lion and always tried hard in his races.
This giant of a horse was a tremendous servant for connections and his win in this race the Ascot Gold Cup will live long in the memory. A certainty for the favourite winners list.
Rite Of Passage, 2010
Rite Of Passage makes the list for a variety of reasons. Firstly, given he was ridden to success in the Gold Cup by the late-great Pat Smullen and secondly, provided Dermot Weld with a first success in the race.
He often mixed it over hurdles and on the Flat and he claimed this race by a neck, his biggest win of his career. He engaged in a great battle with Age Of Aquarius and just got his head in front at the line to lift the prize for his powerful connections and top-class rider.
The race was run at a helter-skelter pace and he coped with everything asked of him on the day to spring a minor surprise at double-figure digits. His performance was even more unique as it came on just his third start under flat rules and was even placed at a Cheltenham Festival over hurdles as well.
He wasn’t the easiest to train but when we saw him he was good and after finishing third on his reappearance almost a year after his Gold Cup win, he returned to Ascot to win his final career start a year later in the Qipco British Champions Long Distance Cup.
Yeats, 2006, 2007, 2008 & 2009
The most decorated horse in the history of the race is four-timer winner Yeats, who won this between 2006 and 2009 and it was a credit to connections that he managed to bring his A-game to the race each and every time.
He was trained by Aidan O’Brien and amassed over £1 million in earnings. He won his first Gold Cup by four lengths before becoming a dual winner a year later, when sent off odds-on favourite and beating Geordieland by a length and a half under Mick Kinane for a second time.
In the 2008 renewal, he was ridden by Johnny Murtagh and beat Georgieland again but this time much easier by five lengths, arguably his best of his three wins in the race to the date, becoming the first horse since Sagaro in the 70’s to win the race three times.
His final season in training got off to a low-key start, as he was beaten over 30 lengths on his reappearance but connections managed to get him to peak on the biggest day again, as he landed the Gold Cup for a fourth time, beating Patkai by over three lengths and becoming the first four-time winner of the race.
He ran two more times afterwards without success but his achievements in this race make him one of the greatest stayers of all time and the fact he ran in this four times and was never beaten makes him a definite choice for the list as one of my favourite winners of the race.
Finally, the most famous result in the history of the Gold Cup was Estimate’s success a decade ago, where she provided the Queen with an emotional success, who had the biggest smile on her face when seeing her top-class stayer take the spoils.
In turn, she became the first reigning monarch to have a horse win the Gold Cup in its 200+ year history. She was ridden by Ryan Moore and always tracked the pace before being produced to lead over a furlong from the finish.
Despite being challenged by Simenon, this filly responded to Ryan’s urgings and battled to a neck success. She won one more time afterwards, which came in the 2014 Doncaster Cup but undoubtedly her career-defining success was in the Ascot Gold Cup.
Her success in the race was one of the best moments in the history of Royal Ascot as the Queen watched her beloved filly take the spoils with the roar of the crowd cheering on as well. The fifth and final favourite winner of the race this decade.
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