A milestone win this week has brought about a new challenge for apprentice Tom Sadler.

Sadler landed his 20th metropolitan winner on Wednesday which reduces his city claim to 2kg but he'll get one last chance to make an impact with a 3kg allowance at Caulfield on Saturday.

It's an opportunity the 18-year-old wants to make the most of before he embarks on the next challenge of securing rides without the maximum city claim.

Sadler has six rides at Caulfield including two for trainer Anthony Freedman.

"I'm hoping it's not going to be too difficult with a two-kilo claim," Sadler said.

"I hope that if I can get a couple of winners on Saturday, now that I have outridden my three-kilo claim, that I'll still get a bit more support."

Apprentices are always in demand through winter but Sadler says he needs to be riding well for trainers to opt for him over riders who can claim 3kg.

"Trainers are pretty keen to take the three (kilos) off, they do see quite a large difference between three to two," he said.

"But I'm sure if I continue to ride well and make good connections with trainers like Robbie Griffiths, who I rode the winner for (on Wednesday), and Anthony Freedman who I've got two rides for on Saturday, I'm hoping they can keep putting me on."

His rides for Freedman are on stakes-winning mare Crucial in the Charlie Agius Handicap (1600m) and Benenden in the Melinda Rea Handicap (1600m).

Crucial was beaten 1-1/4 lengths when sixth in the Group Two Queen Of The South Stakes (1600m) in Adelaide last start, and Sadler was happy to learn he'd be riding the mare.

"She's drawn a good gate and it looks like it's going to work out pretty well just to get a bit of cover," he said.

Sadler believes three-year-old Benenden can bounce back with an improved run after racing wide last start when well-beaten at Caulfield.

His mounts also include Bonnie Mac for Mike Moroney and two-year-old Throw The King, trained by his father John Sadler, in the opening race which is a non-claiming race.