The 43-year-old is on course to tick off his latest marker on Sunday, when he’ll become the first driver in the category’s history to start 600 consecutive championship races.
While stressing that he does not take milestones for granted, the Team 18 driver has mixed feelings over this particular number.
“It’s kind of a good memory and a bad memory,” 2015 Supercars champion Winterbottom said.
“The reason I don’t have more consecutive starts is because of the grate coming through the bottom of the car in China. That cost me about 30 extra consecutive starts!”
Winterbottom refers to a scary moment during the Aussie category’s sole visit to the Shanghai International Circuit in 2005.
The underside of Winterbottom’s Larkham Motor Sport Falcon was torn apart when it struck a drainage grate that had been dislodged by a preceding car.
Winterbottom was lucky to escape injury in the incident, as the grate cut through the car mere millimetres from the driver’s seat.
Nineteen years later, Winterbottom chalks up the 600 marker at a time when he’s trying to hold onto his seat for 2025.
The veteran is one of a number of out-of-contract drivers amid a swirling silly season, but cuts a relaxed figure when asked about the future.
“There’s always chats, but nothing’s ever done until it’s done, is it? We’ll see how we end up and what happens,” he said.
“But that always happens every year, even when you’ve got a contract, we see that in the sport a lot.”
When asked if there’s a timeline on getting a deal done, Winterbottom said: “Hopefully by January 1 we’ll have an idea!
“But we’ll go through it. You always go through it and when there’s something to say, you’ll say it, and when there’s nothing to say, you say nothing.
“We’re just at that point at the moment.”
Winterbottom makes clear that his preference is to remain a full-time driver with Team 18, amid a season that has included two podium finishes.
He enters this weekend’s Tasmania SuperSprint 14th in the championship, one place clear of Team 18’s 2024 recruit David Reynolds.
“I’m still driving well,” said Winterbottom. “Dave and I are so close and you forget very quickly that the guy I’m benchmarking against dominated the back end of last year (with Grove Racing).
“Team 18 is a great team, Charlie (Schwerkolt, team owner) is a great guy to race for and it is a team on the up.
“We’re going to have our rough days but on our good days, we’re good enough to win, so there’s light at the end of the tunnel… it’s definitely headed in the right direction.
“I hate starting things and not finishing. Two podiums this year, it’s been better than last year, even though the (championship) position is not. But we’re making progress.
“I love racing for Charlie, he’s a great guy who deserves success. I’d hate to leave and the team kicks its goals and kicks on because they are going to get there.”