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Apprentice jockey Chelsea Baker celebrated one of her biggest career highlights when she partnered $1.80 favourite Sir Simon to victory in the Cressy Chaff Cutters Jim Osborne Longford Cup (1800m) on Monday afternoon.

Well-supported after $2.40 was available on race morning, Sir Simon took up his customary position leading the field, passing the winning post on the first occasion, and from there, he always travelled like the winner, eventually crossing the line 1.5 lengths clear of Page ($8) with Vintage Diesel ($8.50) a further length back in third.

The win was Chelsea Baker's fourth aboard the John Keys-trained 10-year-old gelding.

"It was very exciting to win my hometown cup and pretty special for it to be on Sir Simon, I love that horse," said the elated jockey.

"He got a nice lead in front and a bit of a cheeky sectional from about the 1000 (metres), and when it was time to improve, he did it nicely.

"The margin wasn't huge towards the end there, but he's one of those horses; he would've kept kicking if he had to; he knows his job."

Sir Simon was Baker's only winner on Monday's seven-race card, but it could've easily been more, having been on the wrong end of photo finishes aboard both The Tazwegian (race 1) and Thunberg (race 5).

"I thought Thunberg had won, to be honest, and then the first was a photo as well.

"I got the main one, though, so it was still a great day."

All seven races at Longford were won by apprentice jockeys, a by-product of Siggy Carr and Mehmet Ulucinar being the only two senior riders at the meeting.

Hannah Le Blanc and Taylor Johnstone both rode doubles and as is so often the case at the New Year's Day meeting, Longford trainer John Blacker took training honours with wins for Puma and Alpine Affair.