King Charles’s one time horse racing rival and legendary broadcaster, Derek ‘Tommo’ Thompson, 74, is set to retire.
While the monarch fondly remembers being pipped to the post some 45 years ago, Queen Camilla is said to be less sanguine.
Thompson, a racing presenter and former amateur jockey, will commentate on his last race at Wolverhampton on Tuesday night.
As a young man, Thompson famously triumphed over the then-Prince during a charity flat race at Plumpton in 1980.
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|King Charles finished second being Derek ‘Tommo’ Thompson in 1980 during his stint as an amateur jockey
On the day, Charles was making his debut at the races during his short stint as an amateur jockey.
The future King’s first shot of glory was quickly cut short as Thompson romped to victory.
Despite a future appearance at the Cheltenham Festival, Charles would only secure one more second place finish and no victories in his short career in the saddle.
"I beat the future King," Thompson fondly recalled.
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|Derek ‘Tommo’ Thompson will retire after 60 years in sports broadcasting and a one time rivalry with the then Prince Charles
Far from looking back bitterly at his denial of glory, King Charles often humorously reminisces about the day with Thompson.
"And I remember at Royal Ascot last year, we were having a chat, and I said, 'sorry, Sir. I beat you all those years ago,’" the broadcaster recalled to Freebets.com.
The King was said to reply happily: "Don't worry. I forgave you. Don't worry,"
However, Queen Camilla quickly cut in with humorous warning: "But I haven't Tommo!"
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|Charles was a keen horsemen in his youth, and we denied his closest attempt at a first place finish by Thompson
"We always joke about it, but it was an incredible day. I'll never forget it," Thompson reflected joyfully.
Celebrating the moment earlier this year, the broadcaster wrote on X: "King Charles The Second! 45 years ago today I beat Prince Charles into second place at Plumpton.
"His Highness was 13-8 favourite on Long Wharf; I was on 14-1 outsider, Classified, trained by Nicky Henderson. The highlight of my racing career and the only race I ever won!"
Along with the post, he shared a collage of newspaper headlines from the day covering his triumph.
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|The King often happily reminiscences about the race with Thompson
On Tuesday, Thompson will draw his legendary 60 year career in racing broadcasting to a close.
He became one of the most recognisable faces in horse racing, featuring on BBC radio, ITV, Channel 4 and Sky Sports during his time.
Thompson was even one of the three who attempted to negotiate the release of the racehorse Shergar, after the 1981 Derby winner was kidnapped.
Elsewhere in royal racing circles, the King and Queen were dealt bitter disappointment at Royal Ascot this year as their horse, Reaching High, finished a disappointing ninth in the The King Charles III Stakes.