A snake bite, asthma and a lung infection almost ended his career, but Bootlegging has bounced back to cause an upset in a Sydney Highway race.

Kathy O'Hara guided Bootlegging ($71) to win by half a neck after settling three-wide towards the back in Saturday's Highway Plate (1600m) at Randwick.

It hasn't been an easy journey for the five-year-old gelding, whose owners have been patient over the years but wanted to sack him a couple of months ago because of persistent problems.

"He's had a lot of issues. He's been bitten by a snake and nearly died. He's had a torn suspensory, he got asthma, and had three months in the paddock then he got a lung infection," Canberra trainer Norm Gardner said.

"That's why he's this age and had 18 starts. Every time I get him fit something goes wrong with him."

With the gelding finally in peak fitness, Gardner decided to back him up from his Canberra race last week, when he finished third.

The owners' perseverance paid off, with Bootlegging collecting almost $35,000 for his Highway win.

"Great prize money. Wish I owned him," Gardner said.