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Victoria Pendleton exceeded all expectations by finishing fifth on Pacha Du Polder in the St James's Place Foxhunter Chase at Cheltenham.
Pendleton gave the Paul Nicholls-trained nine-year-old a very patient ride and was stone last for the first mile.
As the race began to evolve, Pendleton, a double Olympic cycling champion, began to move through the field with style.
Dependable in the jumping department, Pacha Du Polder was making lengths at some fences but turning into the straight Pendleton still had plenty of horses in front of her.
As Nina Carberry brought Enda Bolger's champion hunter On The Fringe (13-8 favourite) through to beat Marito by a neck, Pendleton stayed on strongly to complete an afternoon to remember.
Pendleton, whose mount earned £936 in prize-money for fifth, said: "I can't believe how nice the crowd has been, I'd like to thank Alan and Lawney Hill, Andy Stewart (owner) and Paul Nicholls, they've made this all possible.
"I feel honoured to have been given this opportunity. I think it's one of the greatest achievements of my life, a special achievement."
Victoria Pendleton will ride Pacha Du Polder at the Cheltenham Festival on Friday week.
The dual Olympic cycling champion will partner Pacha Du Polder in the St James's Place Foxhunter Chase on Friday week.
Pacha Du Polder's trainer Paul Nicholls and a team of experts made the decision to allow the 35-year-old the chance to fulfil her dream of appearing at next week's Festival.
She said: "We have always had the extremely ambitious target of riding competitively in the Foxhunter as our goal, so to be announcing that I have achieved this goal is a truly amazing feeling."
Victoria Pendleton's Cheltenham Festival dreams suffered a potential jolt after she was unseated in a point-to-point at Kingston Blount on Saturday.
Just days after winning a first race as a jockey at Wincanton, the double Olympic cycling champion was riding the Alan Hill-trained Supreme Danehill when she lost a stirrup after jumping the third fence from the finish and came out of the saddle.
Hill's wife, Lawney, has been one of Pendleton's chief mentors during her Betfair-backed 'Switching Saddles' challenge since it was announced last March that she would make the transition from velodrome to racecourse.
She said: "Unfortunately she's had a fall, but she got up and walked away and is perfectly all right.
"The horse pitched on landing after jumping the third-last. She did well to stay in the saddle, but unfortunately she lost one of her irons, became unbalanced and gravity won."
Victoria Pendleton made every yard of the running to notch her first win as a jockey aboard Pacha Du Polder in the Betfair Switching Saddles Hunters' Chase at Wincanton.
The dual Olympic cycling champion was unshipped from Paul Nicholls' charge on her first start under National Hunt Rules at Fakenham just under two weeks ago, but the duo made no mistake this time.
Sharply away, Pendleton survived a couple of sticky leaps to triumph aboard the 5-4 favourite, running out a 29-length victor.
Her task was somewhat eased when Gauvain, who looked a likely rival, crashed out at the sixth, but Pendleton herself had to survive a slightly shaky jump at the eighth as well as a slow leap at the 10th.
However, she managed to get Pacha Du Polder back on an even keel before kicking for home with two to jump.
She negotiated both of those obstacles with the minimum of fuss, cruising home from Big Fella Thanks to a warm reception from the Wincanton crowd.
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Olympian Victoria Pendleton posed with a group of Beefeaters outside Buckingham Palace after receiving her CBE from the Queen.
Olympic gold medal-winning cyclist Victoria Pendleton has been awarded a CBE by the Queen during an investiture ceremony at Buckingham Palace.
Pendleton retired after the London 2012, but her haul of titles stands at two Olympic gold medals, nine golds from the World Championships and podium-topping results in the Commonwealth Games and European Championships.
Designer Stella McCartney also received an honour today - an OBE for services to fashion.
McCartney, who designed Team GB's kit for the London 2012 Olympics, said before the ceremony she felt "really proud and really excited and honoured".