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Glen Boss: Jockey, 3 times Melbourne Cup Winner

Professional Australian Thoroughbred jockey Glen Boss will always be remembered for taking the 3200-metre trip around Flemington on Makybe Diva for three Melbourne Cup victories. There is much, much more in his body of work as a rider than just the three Cups. Here is a brief biography that will reveal more about the work of Glen Boss on the track.

Glen Boss was born 21 August 1969 in Caboolture, a suburb of Brisbane. Other sources list Beaudesert as the place that Boss was from. The first town is north of Brisbane, while the second in to the south, but they are close enough to each other that it is entirely conceivable that Glen Boss was born in the one and grew up in the other.

Beaudesert seems more likely as the growing up place, as records indicate that Boss moved to Gold Coast not long after he began his riding apprenticeship in 1986 at the age of 15 and after riding 60 winners in the span of under a year, he moved to Gold Coast, just down the road from Beaudesert.

It is a challenge to write a biography of a jockey while that jockey is still riding. Boss is now 51 and continues to be effective as a jockey, although he could certainly be forgiven if he never again rides a Melbourne Cup winner, let alone ride a horse to three wins.

Boss would require one more Melbourne Cup win to join Bobby Lewis (1902, 1915, 1919, 1927) and Harry White (1974, 1975, 1978, 1979) as the only jockeys to win four Melbourne Cups.

Bobby Lewis, as the span of years for his Melbourne Cup wins indicates, needed four different horses. The most significant of these four Thoroughbreds was 1919 winner Artilleryman.

Harry White had the benefit of Think Big beneath him for the wins in 1974 and 1975, where there is every probability that trainer/part owner Bart Cummings’ riding instructions to White were something to the effect, “Just don’t fall off, mate.” White’s third Cup was on Arwon and his fourth was on Hyperno, another Cummings prepared racer.

Five other jockeys have won three Melbourne Cups. Those five are Jim Johnson (1963, 1968, 1969), William H. McLachlan (1909, 1910, 1917), Darby Munro (1934, 1944, 1955), Kerrin McEvoy (2000, 2016, 2018) and Damien Oliver (1995, 2002, 2013).

With Boss, McEvoy and Oliver still riding, the three could serve as the basis for an interesting racing punt, something like “First to Four Melbourne Cups.”

Glen Boss Riding Career

Glen Boss had enjoyed enough racing success that he was inducted into the Australian Racing Hall of Fame in 2015. Significant Group 1 wins, in additions to the Cups, include three Cox Plates (2005, 2009, 2012) the Golden Slipper Stakes (1995), The Everest, Golden Eagle, Newmarket Handicap and Epson Handicap, all in 2019.

Those nine alone would make a career to incite envy amongst most jockeys, but Boss added the Australian Oaks and the Sydney Cup in 2020.

Technically, The Everest and the Golden Eagle are not classified as Group 1 races, even if the prize money for the two races is well above the Group 1 threshold.

At the time this Glen Boss bio was prepared, late in August of 2020, Boss has this for his stat line: 18,562 starts, 2,384 wins (13 %) and 4,032 places (35%). He is credited with 86 Group 1 wins, 61 Group 2s, 75 Group 3s and 144 Listed Races. Combined, his tally for placings equals 688.

Boss has hauled in over $190 million in prize money. His best earnings season was 2019/20, when he made $18.4 million, but that is what winning The Everest and the Golden Eagle will do for you. He is credited with four Group 1 wins for that season.

From a broader perspective, it would have to be said that his best season was 2012/13, when he won 114 times, including three Group 1, four Group 2, 7 Group 3 and Listed Races on his way to almost $11 million in prize money.

His first Group 1 win was on New Zealand horse Telesto. Telesto was a hard worker, but only won three times from 42 jumps. The first was the Group 3 Craven Plate in 1992. Telesto won the Group 1 Chipping Norton with Boss aboard in February of 1994 at Warwick Farm Racecourse. Next up, he won the Group 1 George Ryder, but this time, Shane Dye was steering. Seventeen additional starts supplied just one second and a couple thirds.

Beating the Odds

Once Glen Boss had established himself in the eyes of the Thoroughbred trainers, he was of course booked for top horses. He has been handed the reins of the favourite over 900 times and won 33.3 percent of those opportunities, a number eerily similar to the generally accepted notion that the favourite wins about one third of the time.

Glen Boss impresses, though, for having won almost 1,400 races at odds ranging from $2 to $6, over 500 times at prices between $6 and $11, well over 200 times riding horses jumping anywhere from $11 to $26, 26 races on horses priced $26 to $51 and seven times from beyond $51.

Glen Boss Significant Wins

It is not possible in this space to list all of Glen Boss’s major wins, but here is some additional detail about the big wins mentioned earlier.

1995 Golden Slipper Stakes

This is the first big win by Boss. It is a Group 1 sprint of 1,200-metres run at set weights for colts and geldings. With the possible exception of the Magic Millions 2YO Classic, it is the juvenile race any jockey would love to win. Possibly more so, in fact, as the Magic Millions is restricted to horses from the Magic Millions Sale, while the Golden Slipper is open to any, based on merit.

Boss rode Flying Spur in the race. Flying Spur was a good horse that went on to win beyond his Golden Slipper win, while many two-year-olds often vanish into obscurity.

The pair jumped from the rail and beat none other than the legendary Octagonal by a head. They jumped $26, beating several shorter priced horses. The race had an all-star lineup of jockeys, including Shane Dye, Mick Dittman, Damien Oliver, Larry Cassidy and Chris Munce, to mention a few.

Melbourne Cup 2003

Makybe Diva was one of a kind and needs little by way of introduction.

Boss raced Makybe Diva 16 times and won some races that would later be elevated to Group 1, which would have further burnished Boss’s resume.

The 2003 Melbourne Cup win came on the back of a fourth placed run in that year’s Caulfield Cup. The Diva and Boss jumped second favourite ($8) to the favourite Mamool ($6.50), which finished stone motherless under the crop of Frankie Dettori, who as best we know, did not cause any incident that year.

The winning margin was 1.3 lengths to She’s Archie ($41), but from there, there was all sorts of daylight between the first two and the rest of the field.

Glen Boss and Makybe Diva concluded the autumn by winning the Group 1 Sydney Cup and that win is mentioned here because following the campaign, Makybe Diva was taken from trainer David Hall and dropped in the lap of Lee Freedman.

Melbourne Cup 2004

Lee Freedman turned Makybe Diva over to Damien Oliver and Luke Currie for three races. Boss was not on another horse for any of those three races. He and Makybe Diva were reunited for the 2004 Caulfield Cup, where Makybe Diva lost by a short head to Elvstroem, a good horse that could be classified as a Diva slayer, but Elvstroem jumped from the third barrier, while Makybe Diva came out of 17.

Thoroughbred racing was denied the rare Cups Double by a couple of nostrils and a bad draw.

The name of Elvstroem would be mentioned ahead of Makybe Diva on more than once occasion, but in the 2004 Melbourne Cup, Elvstroem ($6) finished over five lengths behind Makybe Diva.

Boss and Makybe Diva ($3.60) won the race by 1.3 lengths from Vinnie Roe.

Melbourne Cup 2005

Boss was nearly deprived of riding Makybe Diva in the 2005 Melbourne Cup. In the lead up to the race, Lee Freedman threatened to hold her out unless the Flemington stewards watered the track, out of concern that the track was too firm for her. She had won the 2003 Cup on a track rated Good 3, but for 2005, historical records place Flemington as Soft 5, a track condition that seemed to suite Makybe Diva throughout her career. Considering that she and Boss had won the 2005 Cox Plate down the road at Moonee Valley just a month prior when the course was rated Soft 7, many view Freedman’s water demand as a stunt, because it is hard to imagine a turf course going from Soft to Firm in the span of a month.

Couple those views with the fact that Makybe Diva was well nigh unbeatable in spring of 2005. She won the Memsie, ran second in the Feehan, won the Turnbull, the Cox and the Melbourne Cup, supporting the suggestion that Lee Freedman was engaging in gamesmanship more credible.

Glen Boss and Makybe Diva ($4.40-fav.) made history that day, beating On A Jeune ($71) by 1.3 lengths. Three wins, all by 1.3 lengths. Glen Boss must have reined her in at the line so the others would not feel badly.

Boss Wins 2005 Cox Plate

The win was mentioned above, but it bears mention here to bring out the fact that Boss and The Diva ($2) won by 1.3 lengths from Lotteria ($21), with the formidable Fields of Omagh ($17) another 1.4 lengths further back.

2009 Cox Plate

Glen Boss was given So You Think for the 2009 W.S. Cox Plate.

Past results indicated that Glen Boss deserved top horses, obviously, and So You Think belongs in that category without a doubt.

Boss and So You Think ($13) came from the seventh barrier, winning by 2.5 lengths from Manhattan Rain ($21), with the favourite, Whobegotyou ($2.80) was four lengths back.

Boss was the first jockey to guide a three-year-old in Australia’s toughest w.f.a. race since Chris Munce steered Savabeel in 2004.

2012 Cox Plate

Ocean Park carried Glen Boss for the win in the 2012 Cox Plate.

Ocean Park jumped $6 and beat Gai Waterhouse’s Pierro ($5.50) by over four lengths, with Chris Munce on the Hawkes’ All Too Hard ($9) in between.

Unlike the Melbourne Cup, Glen Boss needed three different horses to win the Cox Plate three times.

Other Glen Boss Notable Horses

Whether it is the jockey or the horse that deserves the credit is one of those chicken or egg riddles.

Win and the trainers offer top horses. Fail to win and the quality of horses goes down.

Regardless of which camp anyone falls in, Thoroughbred racing is a rare sport that requires much from both horse and rider. While it is possible that Makybe Diva and So You Think could have won with anyone riding, Glen Boss deserves some credit for earning the right to ride the top echelon horses.

Some of the other notable horses Glen Boss has ridden are the earlier mentioned Ocean Park are Starcraft, Eremein, Haradasun, Divine Madonna, Fastnet Rock and Shogun Lodge.

That impressive list now included 2019 The Everest winner Yes Yes Yes and 2019 Golden Eagle winner Kolding, both Chris Waller horses, by the way, another Glen Boss endorsement.

International Riding

Like many Australian jockeys, Glen Boss has ridden in Hong Kong and Japan and he has ridden on dirt tracks, too. He has made many starts in Singapore, a few in Great Britain and even one in the U.S.


The final chapter of the Glen Boss story is yet to be written.

There was a lull at the start of 2016 when Boss was struggling to get rides. He told a reporter, "You'd go to track work and stand in the hut and nobody wanted to put you on. I was gutted.

These days, Glen Boss is back at the top, for how much longer is anyone’s guess, but older jockeys have recently become the cause celeb and with support from trainers such as Chris Waller, Gai Waterhouse and others, it would appear that Glen Boss will have a job for the next couple of years at least.

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