Legendary Melbourne Cup-winning jockey Glen Boss announces retirement

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Glen Boss — who rode Makybe Diva to three consecutive Melbourne Cup wins — has announced he will retire after a Caulfield race meeting this weekend.

Boss guided Makybe Diva to her three Melbourne Cup victories between 2003 and 2005.

He also won a host of other prominent races, including the Cox Plate, the VRC Derby and the Golden Slipper.

The 52-year-old’s final race will be the Zipping Classic at Caulfield on Saturday.


“This decision is something I have been mulling over for the past six months and particularly over the last two or three,” Boss said in an interview with Ladbrokes.

“I’m one of those individuals who is always 100 per cent, chips in all the way, and I made a promise to myself more than a decade ago … that if I got to the point in my riding career when I wasn’t fully committed and all the way in, then it was time to finish.”

Boss said he had begun to face psychological hurdles late in his career.

“I just felt I was slipping a bit mentally,” he said.

“I felt it was the right time because I have so much energy and I want to put all that energy into something else, and that’s what I am doing.”

Boss won the 2020 Cox Plate on board Sir Dragonet.(AAP/Racing Photos: Natasha Morello)

Boss won 90 group 1 races in Australia, highlighted by his Melbourne Cup triumphs.

He also won the 2005 Cox Plate on Makybe Diva, and guided So You Think (2009), Ocean Park (2012) and Sir Dragonet (2020) to victories in the weight-for-age classic at Moonee Valley.

Boss’s wins in Sydney included two Golden Slipper salutes on Flying Spur (1995) and Sebring (2008).

He also rode Yes Yes Yes to victory in The Everest in 2019 and in the same year triumphed with Kolding in the inaugural Golden Eagle.

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