Ted Durcan produced Central City with a withering late run to claim top honours in the Clipper Logistics Leger Legends Classified Stakes at Doncaster.
A field of 16 former jockeys went to post for the popular contest, which has become the traditional highlight on the opening afternoon of the four-day St Leger Festival on Town Moor.
Now in its eighth year, the charity event has raised significant amounts of money for the Injured Jockeys Fund’s Jack Berry House, as well as the Northern Racing College.
Luna Bear and Dale Gibson made an early play for the lead before Detachment and Cheltenham Gold Cup-winning jockey Andrew Thornton, who only called time on his riding career in June, swept clear and looked the likely winner.
However, the Ian Williams-trained 10-1 shot Central City really found top gear in the closing stages of the straight-mile contest and got up to score by a length and a quarter.
Assimile, ridden by last year’s winning jockey Brian Harding, was third.
Durcan announced his retirement from race-riding in February following a highly successful 25 years in the saddle.
The 45-year-old rode a host of big winners, including a St Leger success at Doncaster in 2009 aboard Mastery for Godolphin and Saeed bin Suroor.
His other Classic triumph came on Light Shift for the late Sir Henry Cecil in the 2007 Oaks at Epsom.
He said: “He was a smashing horse to ride. I know he’s only been running over six and seven furlongs, but Ian was adamant he would stay. He travelled lovely and it worked out.
“The horse I had was a smashing ride for a race like that.
“You miss the weighing room and all the banter and the slanging.
“It’s a great afternoon. It’s really well organised and they raise huge amounts of money, so hats off to everyone, all the organisers and the sponsors.”
Thornton said: “I thought I had it and nearly did it.
“Some people say I might have got there too soon, but I might have never got there.
“I enjoyed it and was beaten by one better on the day.
“I loved it and it’s all for a good cause.”