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100 Years of Gold Cup Glory

Posted: Thu, 14th Mar 2024
Graphic promoting the celebration of 100 years of the Cheltenham Gold Cup. Photograph of the Gold Cup Trophy to the tight with hills in the background and text on the left.

This year marks the Centenary of the Cheltenham Gold Cup. A story that began in 1924, the Gold Cup has since mushroomed to become one of the world’s most renowned steeplechases.

Every year, this popular event creates an unmatchable buzz in Cheltenham, as well as the villages that frame it. On Gold Cup day, there’s a sense of celebration in the air as bars and restaurants spill out with revellers. Mill about long enough and you might catch a glimpse of famous trainers and jockeys weaving between the racecourse and town.

With Gold Cup day approaching, lets take a look at the horses and heroes that have made it so iconic.

History of Racing in Cheltenham

Racing in the area dates back over 200 years.

1818 – 1828: Humble beginnings
In 1818, formal horse racing begins on Cleeve Hill, a common area that frames the north-eastern edge of Cheltenham. Over the next decade, horse racing’s popularity grows as well as meetings at Cleeve Hill attracting crowds of 30,000.

1831 – 1907: Gaining momentum
1831 sees a new course established at Prestbury Park following a fire at the grandstand on Cleeve Hill. Cheltenham Races goes on to achieve considerable growth and notable moments follow, including the formation of The Cheltenham Steeplechase Club and the opening of a special racecourse train station catering for both passenger and equine traffic.

The Gold Cup Era

The first Cheltenham Gold Cup was held at Prestbury Park 100 years ago.

1924: First Gold Cup win
In 1924 the Cheltenham Gold Cup commences, and in that year, Dick Rees rides Red Splash to a glorious win. The prize is £685 cash and a trophy comprised of 644 grams of nine carat gold. Dick goes on to become the first jockey to ride 100 winners in a National Hunt season that year.

1964: Securing the future
The Racecourse Holdings Trust (now Jockey Club Racecourses) is established to secure the future of Cheltenham. The group reinvests profits back into British racing to secure its continuing success.

1948 – 1950: O’Brien domination
The early post-war years see Irish trainer Vincent O’Brien land three consecutive victories with Cottage Rake. O’Brien later becomes one of the most successful trainers in the world, which amplifies Cheltenham Festival’s public popularity.

1989: Desert Orchid triumphs
On the day of the 62nd Gold Cup, torrential rain pours over Cheltenham while snow covers Cleeve Hill. Despite this, Desert Orchid steals the cup in a win that defies the odds of the day. The stunning grey gelding is still regarded as one of the greatest steeplechasers of all time.

Post-Millennium

After 2000, Cheltenham Gold Cup plays host to countless heart-pounding wins.

2002 – 2004: Best Mate’s hat trick 
Trained by Henrietta Knight, bay gelding Best Mate scores a hat trick of victories from 2002 – 2004. The Irish horse gains an incredible cult public following, even receiving fan mail at his yard.

2022: First female winner
Irishwoman Rachael Blackmore is the first female jockey to win Cheltenham Gold Cup on A Plus Tard. The moment is seen as the most iconic of Cheltenham’s 100-year history according to a
Betfred survey.

2024: Blackmore strikes again
Rachael Blackmore completes a flawless ride on Captain Guinness to be the first winner of the Betfred Queen Mother Champion Chase. Queen Camilla presents her with a trophy during a ceremony, and describes the win as “Absolutely Fantastic.”

Discover more history with our hideaways


The area surrounding Cheltenham racecourse is one of idyllic beauty thanks to undulating hills, wild woodland and babbling streams. Cleeve Hill for example, where the Gold Cup originated, is the highest point both of the Cotswolds hill range and in Gloucestershire. It offers a breathtaking view to the west, over Cheltenham and the racecourse, over the River Severn and to Wales; and also across to the historic town of Winchcombe. Many of our holiday cottages are burrowed in these areas, making them the perfect base for staying while learning more about the history of the Gold Cup.


Amber Cottage, Cheltenham

A cosy, semi-detached, holiday home built in traditional, honey-coloured Cotswold stone made even more fantastic thanks to shared facilities including an outdoor swimming pool. This special spot was also once part of the stables to a once neighbouring 18th-century coaching inn, with evidence of this time still seen in the cottage’s ancient, exposed beams.

Granary at Hunt Court, Cheltenham
Cosy and chic, the Granary at Hunt Court offers an idyllic escape. Surrounded by peaceful farmland and scenery populated by abundant wildlife, this special spot makes for the ideal place to switch off and relax after a day discovering the chronicles of Cheltenham Festival.

Jasmine Cottage, Cheltenham
A charming, converted barn built in local Cotswold stone and furnished in a country cottage style, Jasmine Cottage was once part of the stables to the once adjacent, 18th-century coaching inn called The Crown, and its exposed beams are a reminder of its rich history.

Hillview Hideaway, Gotherington
A superb, luxury holiday home, Hillview Hideaway is your Cotswold haven for exploring Cheltenham and its history. With its own private patio and a fabulous hot tub, it also has a bright and spacious feel with an open-plan kitchen-dining-living area, and a breathtaking mezzanine bedroom.

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