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Trelawney Stud has a long and illustrious history with the Melbourne Cup. The farm has produced seven winners of the famed race, a claim unlikely to be matched by any other farm in the world. In October of 2010 an event was held to commemorate that achievement and celebrate the 150th running of the race that year. A sculpture by Australian artist Jane Dawson was unveiled and is adorned with the names of the seven successful Trelawney Stud graduates.

In 2014 a crew from Australia's Channel 7 visited with the farm with the VRC Cup escorts to film a segment on the farm and its contribution to the history of the race that stops the nation. Since then Trelawney Stud has been a regular stop on the New Zealand tour of 'The Cup' each year.