Apprentice Jake Bayliss has ended a winning drought and posted his first city double which he hopes is the springboard to a successful winter.

Bayliss rode his first winner in more than two months when he guided the Doug Harrison-trained Alrouz to victory in Wednesday's #Vrcmembers Handicap (2000m) at Flemington.

In a rare midweek meeting staged at Melbourne racing's premier track, Bayliss backed up that win with a narrow victory on Special Miss in another 2000m race.

Special Miss is trained by the apprentice's boss Mick Kent.

Bayliss said the city double was a confidence boost for the winter when apprentice riders are usually in demand.

"This is an industry with plenty of apprentices, and doors open and doors close," Bayliss said.

"Things were drying up a little bit, I wouldn't say badly, but rides can drop off because there's no form behind you.

"But with this double today things should really take off hopefully."

Bayliss was fined $500 a breach of the whip rules aboard Alrouz.

Kent believes if Bayliss, the elder brother of fellow Melbourne apprentice Regan, gets his confidence up he can have a good winter.

"He's a bit of a confidence kid," Kent said.

"This is the time for Jake now. He claims three kilos in town and I think he's one of the better ones going around.

"It was good for him to get back on the board because he hadn't ridden a winner for a while in town and he needs that to get a bit of momentum now going into the winter."