Champion jockey Glen Boss retires

25 November 2021 Written by Lotti Dyer

Glen Boss, one of the most prolific jockeys to have graced the Australian turf, brought the curtain down on his illustrious riding career last month after over 35 years in the saddle.

Boss, who will forever be associated with the unprecedented Melbourne Cup three-peat of champion mare Makybe Diva in 2003, 2004 and 2005, fittingly announced that he would hang up the saddle in an emotional press conference in front of the Flemington Racecourse statue celebrating his most famous equine partner.

"This decision didn't come lightly and it's been in the brewing for the last three months. I just felt that the bar I'd set myself for my whole career was very high, and the level that I want to be at is very high and I felt in the last couple of months I could feel a bit of a shift," Boss said.

"I made a dear promise to myself more than a decade ago that once I got to that point I'd make a decision and stick firm to that decision and I would retire from professional riding and that's where it's all come to a head in the past couple of months. 

"To stand in front of this iconic Makybe Diva statue at what is the holy grail of racing in Flemington is very fitting. She took me on an incredible journey and I was privileged to be a part of that journey."

While his Melbourne Cup success with Makybe Diva may be his most famous feat, he is one of only six riders to ever record 90 Australian Group 1 wins to his name. He retires the equal of another Flemington icon in Roy Higgins, both on 90, with only Damien Oliver (126), George Moore (126), Jim Cassidy (98) and Hugh Bowman (95) ahead of them.

Thirteen of those Group 1 wins came at Flemington: three Melbourne Cups and an Australian Cup in 2005 on Makybe Diva, two Lightning Stakes victories on future stallions Choisir (2003) and Fastnet Rock (2005), an Australian Guineas on Shamrocker (2011), a Mackinnon Stakes success with Casual Pass (2003), an Empire Rose Stakes with Miss Potential (2004), last year's Newmarket Handicap and Darley Sprint Classic double with Bivouac and the Victoria Derby and VRC Oaks once apiece with Hit The Roof (2000) and My Brightia (1996) respectively.

He also won the Cox Plate four times, the Doncaster Mile seven times and the Golden Slipper twice in the 27 years since his first Group 1 win on the Grahame Begg-trained Telesto in the 1994 Chipping Norton Stakes.

Boss, the self-labelled "kid from Caboolture" who rose to the top of the jockey ranks in Australia, was inducted into the Australian Racing Hall of Fame in 2015. His apprenticeship began in 1986 at Gympie with trainer Terry Chinner, riding quarter horses around the dirt tracks of the Queensland bush, before he transferred to Gold Coast mentor Kaye Tinsley.

Victoria Racing Club Chairman Neil Wilson paid tribute to Boss' career, particularly his feats at Flemington.

"It was only fitting that Glen should come back to Flemington, to the scene of his greatest success, to announce his retirement with the Makybe Diva statue behind him," Mr Wilson said. 

"Glen is to Makybe Diva what Jim Pike was to Phar Lap or Hugh Bowman to Winx, and he will forever be a Flemington legend and a champion of the Australian riding ranks.

"No jockey is more closely linked with Australia's greatest race, the Melbourne Cup. Anyone who witnessed Makybe Diva win her third Melbourne Cup will never forget his cool-headed ride, his post-race emotion and his genuine love and affection for her. It is an image that will be forever linked to the race that stops the nation.

"It has been a privilege to see him ride at Flemington for so many years and I am sure that he will be a constant presence trackside for years to come."

He gave 2021 Lexus Melbourne Cup placegetter Spanish Mission a great ride in the Group 2 Zipping Classic (2400m) at Caulfield on November 27, finishing fourth and closing out a brilliant career in the saddle.

That was to be his last ever race ride, however, he has accepted an invitation to ride in Saudi Arabia at the lucrative two-day festival, headlined by the USD$20m Saudi Cup.

Boss will have one last hurrah representing Australia against some of the world's best riders in the International Jockeys Challenge at King Abdulaziz Racetrack in Riyadh, Saudi Arabia on Friday, February 25 2022, ahead of the $31.5m Saudi Cup race day the following day.

Boss’ Flemington Group 1 Winners

My Brightia

1996 VRC Oaks

Hit The Roof

2000 Victoria Derby


2003 Lightning Stakes

Makybe Diva

2003 Melbourne Cup

Casual Pass

2003 Mackinnon Stakes

Miss Potential

2004 Empire Rose Stakes

Makybe Diva

2004 Melbourne Cup

Fastnet Rock

2005 Lightning Stakes

Makybe Diva

2005 Australian Cup

Makybe Diva

2005 Melbourne Cup


2011 Australian Guineas


2020 Darley Sprint Classic


2020 Newmarket Handicap