Cheltenham Festival 2024: 100 Gold Cup Winners Gather to Celebrate Centenary

Some of Jump racing’s most famous names attended Cheltenham Racecourse, as 100 winners of the Cheltenham Gold Cup gathered to celebrate the race’s centenary.

Although a race known as the Cheltenham Gold Cup had existed in the past as a three-mile Flat race in the 19th Century, its present status is very much down to the foresight of Frederick Cathcart, Clerk of the Course and Chairman of Cheltenham Racecourse from 1908 to 1934.

Red Splash won the inaugural running of the Cheltenham Gold Cup in 1924 and was presented with a magnificent trophy comprised of 644 grams of nine carat gold and plated in 18 carat gold to give it a rich colour.

In celebration of Gold Cup 100, all living previously successful Gold Cup trainers and jockeys were invited to Cheltenham Racecourse for a special Legends Lunch on the eve of the 2024 Cheltenham Festival (Monday 11th March).

One jockey in attendance was Simon Sherwood, who partnered the famous grey Desert Orchid to an unforgettable success in the renewal staged on 16th March 1989.

Sherwood said: “Cheltenham is a special place. When you see those gates open through the middle of the winner’s enclosure – it’s something you’ll never forget. To seeing the parting of the waves of the crowd when you walk back in is always great.

“The year Desert Orchid won, I was staying with the Twiston-Davies family up the road and the rain that arrived had not been forecast. It was an absolutely bonkers day.

“Cheltenham is the holy grail and always the target at the start of the season. From December onwards, you start to know which horses are going to be going there.”

Referring to Desert Orchid, Sherwood added: “By time Desert Orchid ran in the Gold Cup, he had already won a Whitbread Gold Cup so we knew he’d get the trip. It was more a case of Cheltenham being a left-handed track.

“I knew if I got within a couple of lengths of the leader going to the last, then I knew he’d have the guts to get up the hill.

“I remember jumping the last, putting my head down and thinking I’ll never have this opportunity again. The crowd was just amazing and to win was just the ultimate. The Queen Mother was here which made it even better – a phenomenal day.

“I am very fortunate and have some very fond memories.”

Perhaps surprisingly, Sherwood retired from the saddle at the end of the 1988–89 season but this was something he had planned in advance.

He explained: “I had been very lucky and just felt I had ticked all the boxes I wanted to tick.

“I was in one piece and although I was only 31, I felt it was time to walk away.

“It was annoying when the thought sunk into my head that I wouldn’t be riding Dessie again but I had made my decision and when you go and change it that is when you usually go and get hurt.

“The only time I really regretted it was when Dessie won the Irish Grand National in 1990. That was a special day and I would love to have been involved.”

Text by Ben Cox. Photograph courtesy of The Jockey Club/David Davies.

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