Jockey Saffie Osborne has a big chance to make British horse racing history in the St Leger on Saturday at Doncaster on board Highwayman.A female jockey has never won any of the British Classics before – the 2,000 Guineas, 1,000 Guineas, Epsom Oaks, Epsom Derby, and the St Leger – and Osborne is looking to change that on board the Joseph Patrick O’Brien-trained colt.Doncaster holds the oldest British Classic, running for the 250th time this weekendGettyThe 24-year-old jockey was handed the ride after O’Brien’s first-choice jockey Dylan Browne McMonagle was ruled out through injury, though he would have likely been on board Enceldaus, who will be ridden by Billy Loughnane chasing Champion Jockey status.The winner of this Classic will get nearly £400,000 and it’s the same trainer of Highwayman.O’Brien also trains Enceladus who’s contending to be the favourite with the Aidan O’Brien-trained Christmas Day.It’s close between those two and Pierre Bonnard who’s not far behind in the odds.Osborne has enjoyed an incredible season, probably her best so far as a jockey.She landed a treble at Ascot on King George day, a double at Glorious Goodwood and winning £143,000 aboard Zigazag Ah in the Weatherbys Super Sprint.‘He looks a really nice horse’Highwayman has proven his stamina winning the Listed Vinnie Roe Stakes at Leopardstown ahead of the St Leger challenge which will also be over 1m6f.Osborne praised the colt after being confirmed for the ride, believing there should be more to come from the three-year-old.She told Racing TV: “He looks a really nice horse and it’s great to get the opportunity.“He won a Listed race last time out and looked to stay the trip well that day, so hopefully the same distance on Saturday will be no issue for him.”Highwayman has been well-backed, into 10/1 from 14’s and was even as big as 33/1 last month.History at Doncaster?History could be made at Doncaster should Osborne win on Highwayman which will be in the 250th running of Britain’s oldest Classic.Hollie Doyle became the first female jockey to place in a British Classic back in June 2022 in the Oaks and the first to win a European Classic, scooping the Prix de Diane (the French Oaks) also in the same month in 2022.Doyle made history in both of those races on board the same horse, Nashwa.Can Osborne follow Doyle in making history in British Classics and go one further to be the first to win?