Shirley (41) won the $15,000 Riverton Cup with Chokullen and was also successful with Thrill Factor and Ruby Ruby.
Ruby Ruby gave Shirley his first training win with his first starter when she was successful at Winton on October 14.
Shirley was handed the reins by his 80-year-old father Gil, who told him it was a good time as the team was strong and would give him a good start to a training career.
Gil was on hand yesterday. He was thrilled for Brent and had his photo taken with the three winners.
Chokullen came along the inner from three back on the turn and drew clear with 80m to run.
Shirley raised his right arm high over the concluding stages and could not wipe the grin off his face on returning to the birdcage.
Chokullen had four starts from the Tim Butt stable and joined the Shirley barn in April last year as most of the owners were from Southland.
He is raced by John Frew and his wife Yvonne, of Invercargill, Graham Barrett, of New Plymouth, Carol McLeay, from Auckland, and the three-person BCC syndicate from Invercargill, managed by Calvin Claridge.
The Christian Cullen-Chokhann 5yr-old was recording his third win and has been placed on seven occasions.
Chokhann is a sister by Vance Hanover to Chokin, the winner of 34 races.
The favourite, Ted West, weakened to fifth in the run home after having the run of the race.
Better To Be Bad stopped on the home turn when resuming from a five-month break.
• The Fiery Ginga continued his superb form with an eight-length win from 60m in the main trot yesterday.
Trainer-driver Alan Clark took the 6yr-old to the front with 2000m to go and he drew clear in the run home.
The Fiery Ginga has recorded four wins and three placings from seven starts this season.
The win yesterday was his 22nd and took his stake earnings to $251,369 for Clark, who races the gelding with his wife, Fiona, and his Dunedin breeder, Steve Thompson.
The Fiery Ginga will now head to the group one $80,000 New Zealand Trotting Free-For-All (1950m, mobile) on New Zealand Trotting Cup day tomorrow week.
He has the gr one $200,000 Dominion Handicap (3200m) three days later on his programme.
He finished ninth in the Trotting Free-For-All last year and sixth in the Dominion. Both races were won by Vulcan.