Cheltenham welcomed some of jump racing’s most famous names on Monday as it hosted a centenary celebration for the Boodles Cheltenham Gold Cup.

All living previously successful Gold Cup trainers and jockeys were invited to a special Legends Lunch on the eve of the 2024 Festival, to toast a race that was established in its current form in 1924, when Red Splash won the inaugural running.

Some legends of the sport have subsequently added their names to the roll of honour, including five-time winner Golden Miller, three-times victors Cottage Rake, Arkle and Best Mate and the only grey to triumph, Desert Orchid.

His 1989 success raised the Cheltenham roof and rider Simon Sherwood was among those to attend the Cheltenham event.

He 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 see 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.”

Desert Orchid – aka Dessie – remains one of the most popular National Hunt horses of all time, plying his trade from two miles up to three and half miles, shouldering monster weights in handicaps alongside competing in Grade One company.

Sherwood recalled: “By the 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.”

Other riders at the event included Rachael Blackmore, the only female jockey to have triumphed in the contest, and Ruby Walsh, who is the most successful Festival rider of all time and partnered Kauto Star to victory in 2007 and 2009, when he became the only horse to regain the title, having lost out to Denman in an epic battle in 2008.