Who are the Biggest Winners from the Cheltenham Races’ History?

Who are the Biggest Winners from the Cheltenham Races’ History? Image of horses racing on grass

The Cheltenham Festival is widely deemed a key event in horse racing that assembles the most superior horses, jockeys, and trainers worldwide. Unique, this festival, with its reputation for fantastic races, acts out the parade of the competitive fire, and these highlight the highest level of jump racing. In this article, we look at the stalwarts of the week that were, and somewhat endearingly, dig into the tales of those who coloured the Cheltenham fields with their everlasting performances.

Major Winners

The Cheltenham Festival, of course, regarded as the most competitive spring event, was where several feats were performed. Those four championships combined are the highest honour that exists in jump racing, and the Cheltenham Gold Cup is indisputably the epitome of that. Here, we bring to light the magnificent horses who have not only emerged winners once but several times, participating in various Gold Cups and, of course, whose names have now been inscribed in the annals of horse racing history.

Golden Miller

There was no other horse that did as well as Golden Miller did in the Gold Cup because, after five victories in a row (1932-1936), he managed to beat everybody else. This world-class feat established Golden Miller as the king of The Gold Cup, being the record-setter of his time, thus showcasing the time of untimed achievements.


Regularly declared as the all-time steeplechasing king, Arkle’s three-in-a-row victories in 1964-1966 are a testament to the level of his talent and endurance. His impact on the history of horse racing is so huge that, as of today, he tops the list of the best-rated FEI jumping horses of all time according to the ratings on the Timeform ranking system.


Cottage Rake

The Gold big snipped from Cottage Rake at three removals in a row between 1948 and 1950 stands out as the evidence of his never-waning spirit and bursting crowd. In this inspiration, he was tutored and groomed by the renowned Vincent O’Brien, herself beginning a new era in Irish Horseracing.

Best Mate

After bagging the EWEC’s Championship in 2002, 2003, and 2004, the Best Mate reigned the racing scene as a dominant champion and earned the public’s hearts. He is still a name that is related to courage and fortitude.


He is best remembered for his triumphs in 1970 and 1971, but his greatest achievement is highlighted by his victory in the Grand National in 1973; this proves his versatility in every field he participated in and became one of the most famous horses in history.

Kauto Star

The achievement which is particularly worth mentioning is the brilliant comeback of Kauto Star who managed to win the Gold Cup in 2007 and take it back later in 2009. He is thus the first and the only horse who has both won and regained the prestigious trophy. His excellent career features variety and winning of races in different categories.

Al Boum Photo

Recent victors, those which have won consecutively in 2019 and 2020, with the Al Boum Photos marvelous back-to-back wins, the latest demonstrates excellence in modern jump racing and the continued attractiveness and competitiveness of the Cheltenham Gold Cup.

Final Thought

The last race on Cheltenham Festival’s agenda that is always looked out for has never failed to send the audience back home with memories that would last for eternity. Topmost among them were jockeys, trainers, and thoroughbreds who exhibited a rare combination of virtues, including the power of determination and skill. For enthusiasts looking to delve deeper into the nuances of horse racing or perhaps even calculate the potential returns on their wagers, a free betting odds calculator can be an invaluable tool. This digital aid offers insights into the dynamics of betting, allowing fans to engage with the sport on a deeper level.

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