Cranbourne trainer Stephen Theodore celebrated a rare city double at Caulfield on Wednesday that provided equal measures of compensation and relief.

While the win by former Rockhampton galloper Last Gift in the Programmed Property Services Handicap (1000m) came as a relief to Theodore, the victory later on the card of Road Trippin' triggered a string of emotions.

Road Trippin' is a brother to the ill-fated and highly-talented two-year-old Crack A Roadie.

One of the most promising of Victoria's early season juveniles, Crack A Roadie had just overcome a series of minor issues when he escaped from his handler outside Theodore's stables, was hit by a truck and killed.

"It was an absolute tragedy," Theodore said as he welcomed back Road Trippin' at Caulfield.

"He had so much promise and we'd just got on top of his problems.

"But I think this bloke can go on with it now. It would be justice."

Road Trippin' took on older horses in the TMB Printing Handicap (1600m) and beat them all convincingly, scoring by 2-1/2 lengths from Infinite Energy with another 1-1/4 lengths to Done Nothin' Wrong.

As well as offering some consolation for the loss of Crack A Roadie, Road Trippin' gave Theodore and his owners the hope of at least a minor spring success.

"I've got the Cranbourne Cup in mind for him," Theodore said.

"I think he can stay and I don't reckon it would be beyond him."

Theodore also took away some hope of another winner for the owners who endured the demise of Crack A Roadie.

"I have another one out of the same mare who is going pretty well," he said.

"We all deserve some luck."

Earlier in the program Theodore greeted the win of Last Gift with as much relief as joy.

At his first three starts for his new trainer, the former North Queensland galloper had finished last twice and second last once before scoring at Swan Hill ahead of Wednesday's victory.

"I've never had a horse from Rockhampton before .... I should have turned him straight out when he came to me," Theodore said.

"We didn't make the best start with him, but he's found his form now."

Last Gift, the $3 favourite, led throughout and just lasted to beat Zedi Knight ($3.70) by a short neck with Shadowfax ($7.50) third.