The fledgling partnership between trainer Bjorn Baker and high-profile owner John Singleton celebrated its first city victory when Killcareless scored at Warwick Farm on Wednesday.
The filly is the first horse Baker has prepared for Singleton, who severed his ties with trainer Gai Waterhouse following a public spat over star mare More Joyous in April.
Baker was among the beneficiaries of the split and he was thrilled Killcareless was able to deliver a first victory for the flamboyant owner.
"It's the first one I've trained for him," Baker said.
"She was a high-priced yearling so it was good to get a result like this.
"It was a good win and a good way to start the day."
Killcareless stalked leader Madam Devine, hitting the front in the straight and fighting resolutely to hold out debutante Wordplay by a neck in the Australian Turf Club Handicap (1300m).
Baker was unsure of immediate plans for Killcareless, content to let the dust settle before making any decisions.
"She's come a long way this preparation. Now she's won a race here we will have a think about what we do."
Waterhouse had to settle for third with Madam Devine but she was back in the first placegetter's stall a race later when Mr Jackman led all the way in the TAB iPhone App Handicap (1300m).
The three-year-old had picked up a cheque in all four previous starts without winning but he finally got his moment in the sun when he defied all challengers to score by 1-1/4 lengths over El Sasso.
Waterhouse predicted the form out of the two three-year-old races on Wednesday would stack up.
"These three-year-old races are quite above average," she said.
"In 1995 Nothin' Leica Dane came out and won at this meeting so it has been quite a formidable meeting in the past."
Meanwhile, Waterhouse's appeal against two separate fines imposed over the More Joyous saga will now be heard on September 27.
The trainer was penalised for not informing stewards there were fitness issues with More Joyous before the Queen of the Turf Stakes and the All Aged Stakes.