The Kyneton trainer won four of the six races, including the $17,000 Tocumwal Gold Cup.
He also walked away with a third placing from the five races contested.
The $2 favourite Uptown Lilly had no trouble in the main race winning by 3 lengths from Tableaux and third placed Victorian Crown.
The four year-old mare went into the race with decent form, having been placed at her previous three starts, and a lower weight of 55 kilograms helped over the 1300m.
Victorian Crown has been listed to run in tomorrow’s Anzac Day Cup in Deniliquin.
The win by Uptown Lilly gave jockey Blaike McDougall his third win of the day.
Osborne said winning the Tocumwal Gold Cup was another nice addition to his cabinet.
‘‘It was pretty easy in the end but there’s a lot of hard work and planning that goes into it and we thought it was a good option for her,’’ he said.
‘‘She’s been knocking on the door and it was time to give her a good confidence booster.’’
Uptown Lilly’s past three placings were at Bendigo, and in November she was placed at Moonee Valley.
‘‘It feels good to win any race, particularly a cup race,’’ the trainer said.
‘‘We’ve been fortunate to win a few cup races over the years and this is just another we hadn’t won, so it will be good to put on the mantle piece with the others.
‘‘I have no idea where we’ll go to next with this horse; we’ll let her cool down and go from there.
‘‘It’s been a great day and the horses seem to be in good races, which helps the cause and everyone has done their job,’’ Osborne said.
Jerilderie trainer Phil Sweeney took the honours in race two with his five year-old gelding Bezazzalled winning by 1 lengths to Destiny’s Revenge and Osborne’s Sonaisali.
Destiny’s Revenge was one of two second placings for Wangaratta trainer Russell Green, who had Tableaux in the Gold Cup.
Mistake won race one, beating favourite Wonaeamirri by 1 lengths, from third placed Eagle Point.
Jerilderie trainer Ross Purcell rounded out the first four with Smokin’ Coni running a strong race for the outsiders.
Osborne’s Sinnamon Lane won easily by 2 length in the third race. Ultimate Destroyer and Destitution finished second and third respectively.
Jerilderie jockey Brooke Sweeney proved why Magic Pegasus was the $2.10 favourite with a one length win in the last race.
Purcell and the Sweeney partnership (Brooke and Phil) will also feature in tomorrow’s Anzac Day racing in Deniliquin.
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