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Birthday boy Glen Boss hopes to turn back the clock more than two decades when he rides Love Shack Baby in the $150,000 Rowley Mile at Hawkesbury on Thursday.

Boss, who turned 50 on Wednesday, has recently resettled in Sydney after a long and successful Singapore sojourn.

He won the Listed Hawkesbury race in 1996 for trainer Clarry Conners on Headstrong, not long after he made a career changing move from Queensland to Sydney.

"I hadn't long moved to Sydney from Queensland when I won that Rowley Mile," Boss recalled. "It would be nice to do it again."

"I'm delighted be back riding in Sydney. Racing here is in terrific shape and I'm enjoying the challenge again."

Boss clinched his third Coffs Harbour Cup win on the David Pfieffer-trained Love Shack Baby on August 1.

"Obviously it's a step up in class but Love Shack Baby is racing well and comes in on the minimum weight (54kg) even though he went up eight benchmark points for his Coffs win," Boss said.

"He is tough and is such a consistent horse. He is going to give punters who back him a good run for their money.

Love Shack Baby beat the Queensland galloper Looks Like Elvis at Coffs Harbour and that horse bolted in at Eagle Farm last Saturday.

Boss will always be remembered for his three Melbourne Cup victories on the mighty Makybe Diva (2003-05) and earlier this year claimed a seventh Doncaster Mile win on Brutal during The Championships at Randwick.

He has also won two Golden Slippers (Flying Spur in 1995 and Sebring in 2008) and three Cox Plates (Makybe Diva, 2005, So You Think, 2009 and Ocean Park, 2012) during an illustrious career.

The talented UK import Supernova (Brenton Avdulla) begins his spring campaign in the Rowley Mile while Sydney's training supremo Chris Waller has opted to put a tongue tie on his sole Rowley Mile representative Brimham Rocks.

Waller nominated eight horses but decided to rely on Brimham Rocks, who hasn't raced since failing in the Sydney Cup over 3200m at Randwick in April.

His rider Kerrin McEvoy won the 2014 Rowley Mile on Mr Chard for Tony McEvoy while Waller is seeking his fourth success in the Hawkesbury feature, having won with Snow Alert (2010), McCreery (2016) and Mister Sea Wolf last year.