Great St Leger upsets: when underdogs beat the form book

From a 200/1 shock in 1822 to a Triple Crown denied in 2012, Doncaster has a habit of humbling favourites.

Split image transitioning from a sepia-toned 19th-century racing engraving on the left to a modern close finish on the right, banner text reading "Great St Leger Upsets — From a 200/1 shock to a Triple Crown denied"

No Classic has a longer history of springing surprises than the St Leger. Three results in particular still stand as reminders that the form book counts for less at Doncaster than almost anywhere else. They are part of the 250-year story we told earlier this year.

Theodore, 1822: the biggest shock on record

Theodore remains the longest-priced winner in the race’s history. Sent off at 200/1, he is still, over two centuries later, the benchmark for a Leger upset. Details from the era are sparse, but the result itself has never been disputed. He still sits at the top of our complete list of St Leger winners.

Cut Above, 1981: beating a Derby winner and a legend in waiting

Cut Above won at 28/1, but the real story was who he beat. Shergar, sent off favourite fresh from his historic Derby romp, could finish only fourth, with Glint of Gold also behind the winner. It remains one of the sport’s most quoted reversals of Derby form.

Encke, 2012: stopping a Triple Crown

Encke’s 25/1 victory carried more weight than any other Group 1 result that season. Camelot arrived at odds of 2/5, unbeaten in the Guineas and the Derby and one win away from the Triple Crown, a feat we explored in full in our Triple Crown feature.

Godolphin’s pacemaker Dartford set up a strong pace. Camelot never found the space to strike, and Encke held on by three quarters of a length. It was the sixth St Leger win for Sheikh Mohammed’s operation, and the longest-priced winner since Cut Above three decades earlier.

Why the Leger keeps surprising

The St Leger is three furlongs further than any other Classic, run at the end of a long season. That combination tests stamina and readiness in ways the shorter Classics never do. It has a habit of finding out the horses the market trusted most. That is exactly why Doncaster remains must-watch racing every September.