The 250th running of the St Leger was always going to have a place in racing history. By the time Highwayman crossed the line at Doncaster on Saturday, 12th September 2026, it had become historic for a reason nobody could have known when the season began.
Saffie Osborne rode the Joseph O’Brien-trained Highwayman to a two-and-a-half-length victory, becoming the first female jockey ever to win one of Britain’s five Classic races.
It was a major personal first for the 24-year-old, but also a landmark result for British flat racing. Female jockeys had won the Grand National, major Group 1 races and Classics elsewhere in Europe, but the 1,000 Guineas, 2,000 Guineas, Oaks, Derby and St Leger had remained untouched.
A St Leger That Already Had Plenty Going On
Even before Osborne entered the record books, the 2026 St Leger had plenty around it, largely the fact that is was the 250th running of Britain’s oldest Classic, first staged in 1776. That, and Derby winner Christmas Day was trying to add a second Classic to his season.
The build-up had provided plenty of drama, with the Great Voltigeur winner Maltese Cross looking to be a major St Leger player after beating Pierre Bonnard and Christmas Day at York. However, connections opted to miss Doncaster and head towards the Prix de l’Arc de Triomphe instead.
That left Christmas Day, Pierre Bonnard and Joseph O’Brien’s fast-improving Enceladus among the main names, with Christmas Day and Enceladus the two switching back and forth at the top of the betting markets.
The O’Brien family eventually supplied six of the 11 runners, with Aidan saddling Christmas Day, Pierre Bonnard, Amelia Earhart and Action, and his son Joseph with Enceladus and Highwayman.
The Betting: Christmas Day vs Enceladus
As with any major race, the market changed plenty in the days before the starting tape went up.
Enceladus was one of the biggest horse racing market movers, with firms cutting him from 5/2 to 15/8 during the week, briefly making him the favourite. However, Highwayman was quietly attracting his own support.
He had been available at 33/1 in the ante-post markets, was cut from 14/1 to 10/1 by some bookmakers during St Leger week and was 12/1 with some firms after the declarations. His recent improvement over longer distances was clearly being noticed.
Late money swung things back towards Christmas Day, though, and the Derby winner eventually started the 7/4 favourite. Enceladus was 5/2, Pierre Bonnard 3/1 and Highwayman went off at 11/1.
It turned out the support for Highwayman had been well placed.
How the 2026 St Leger Unfolded
Christmas Day broke well and briefly went into the lead after Action was slow away, but Aidan O’Brien’s pacemaker soon worked his way forward and took over after around two furlongs.
Highwayman was much closer to the pace than Osborne had expected to be, and rather than fight him, she allowed the colt to travel comfortably in a prominent position.
As the field turned into Doncaster’s long straight, Action began to weaken and Christmas Day was asked to go forward, but he just didn’t have it in the tank.
Hatteen moved up strongly around three furlongs from home, but Highwayman was travelling even better, and when Osborne moved past him, suddenly the race began to look very different.
Highwayman beat Enceladus by two and a half lengths, giving Joseph O’Brien a St Leger one-two. Amelia Earhart was another four and a quarter lengths away in third, with Alderman fourth. Pierre Bonnard finished sixth and Christmas Day faded to ninth.
Saffie Osborne Gets Her Classic Moment
Osborne did not even know she would be riding Highwayman at the start of St Leger week.
She said after the race that she had no ride in the St Leger on Monday and found out on Tuesday that she had been booked for Highwayman. It was also her first Group 1 victory.
Osborne has been one of the rising names in British Flat racing for several seasons, but Doncaster moved her career onto another level. As she put it afterward: “This is the kind of thing that changes your life.”
She now joins the likes of Rachael Blackmore, who became the first female jockey to win at Aintree when Minella Times took the 2021 Grand National.
Hollie Doyle had also become the first woman to be placed in a British Classic and won the French Oaks aboard Nashwa in 2022.
Osborne has now added another first, as no woman had ridden the winner of a British Classic before Saturday.
Highwayman’s Remarkable Rise
Highwayman’s part in the result should not be lost in the attention around his jockey.
His early form gave very little hint that a Classic winner was waiting to appear, given that he finished ninth, 15th, 11th and eighth on his first four starts and was sent off at 250/1 for a Naas maiden in June.
Then Joseph O’Brien stepped him up in distance, where Highwayman won a maiden over an extended mile and three furlongs at Killarney by nine lengths before going to Leopardstown and winning the Listed Vinnie Roe Stakes over the St Leger distance by two and a quarter lengths.
He arrived at Doncaster officially rated 101, and for comparison, Enceladus was rated 112 and Christmas Day 118.
Ultimately, Highwayman simply improved again when it mattered most.
Another St Leger for Joseph O’Brien
The result also added to Joseph O’Brien’s record in the race. It was his second victory in the race as a trainer, having won it as a jockey aboard Leading Light for his father Aidan in 2013.
Seven years later, he trained Galileo Chrome to win the race in 2020, and now he has trained the first two home in the 250th running.
In a week that began with much of the talk centred on whether Derby winner Christmas Day would stay, whether Enceladus was the next big improver and whether Aidan O’Brien could add another St Leger to his record, it was instead an 11/1 chance who had been 33/1 a few weeks earlier who won comfortably.
And after 250 runnings of the St Leger, Saffie Osborne became the first woman to ride the winner of a British Classic.
