Two former winners of the Underwood Stakes have fought out a thrilling finish with veteran Black Heart Bart prevailing in a major upset in the Group One race at Caulfield.

Black Heart Bart ($101) won the 1800m weight-for-age race in 2016 for Darren Weir and, now under the training of Lindsey Smith, held off a determined bid from last year's winner, the $2.50 favourite Homesman, to win by a short neck.

Another comeback veteran Gailo Chop ($26) was 1-1/2 lengths away third.

Black Heart Bart was retired after finishing 16th in last year's Toorak Handicap with a number of issues.

Smith set about resurrecting the career of the gelding who was last successful in the 2017 Futurity Stakes at Caulfield, one of four Group One victories the now nine-year-old won during the 2016-17 season.

He was required to pass a number of veterinary tests before Racing Victoria stewards would pass him to race again and even Smith was questioning whether Black Heart Bart would make it back to the racetrack.

It wasn't until Black Heart Bart won a barrier trial at Cranbourne last month that Smith considered the gelding a racing proposition, and only then one race at a time.

"Before he trialled I started to doubt, but then he trialled well," Smith said.

"His first race was good but then his second run was plain but we thought getting him up to the 1800 metres would be good as he wouldn't be chasing all the time.

"It's a good result."

After his long absence Black Heart Bart finished eighth in the Memsie Stakes (1400m) at his first run back before running 11th in the Sir Rupert Clarke Stakes (1400m) eight days ago.

That was a run that showed jockey Brad Rawiller, Black Heart Bart was nearing his best.

"Even though those two runs might have looked a bit plain, he was warming up and I've been happy with him," Rawiller said.

"Today, the whole way through the run I was thinking 'geez, we're going to be in this'."

Homesman's jockey Ben Melham was disappointed to be beaten but thought it was a gallant performance.

"There was a lot more horses press forward than I anticipated early but they were too quick for me and I didn't want to be working up the hill," Melham said.

"From the wide alley he tucked in and I thought he had a good run but he got beaten by a good horse on the day."