Wellington-based Cheeky will take another shot at a Sydney race but hobby trainer Cecil Maxwell insists they're just having a bit of fun.

The three-year-old gelding hung in during a Highway Handicap (1200m) at Randwick in June and came fifth under jockey Daniel Pitomac.

"It was a good run, I thought," Maxwell told AAP.

"The jockey said if he hadn't have hung in he would have been right, so we'll see what happens this time."

Pitomac will be aboard Cheeky for their second city attempt - the TAB Highway Handicap (1250m) at Canterbury on Saturday, after riding him to victory at three country races in May and June.

"He knows the horse, he knows what his little quirks are. He rides him all the time so we'll just take him down with us," Maxwell said.

"We'll just have a bit of fun and see what happens."

Maxwell said wet weather would not dampen their chances on Saturday.

"It was a heavy nine when he went down to Randwick and he handled that all right," he said.

Cheeky doesn't seem to mind the five-hour journey from Wellington to the big smoke, Maxwell said.

"He's good, he's had no trouble. We just put him on the truck and away we go," he said.

"He enjoys doing whatever we want to do, he just does things to please you, I think."

Cheeky is still living up to his name, Maxwell said.

"He was always wanting to bite you and play with you and follow you around all the time, so we'd say, `You're a cheeky little thing,' and that's how he got his name," Maxwell said.

"He's still the same."