Jamie Whincup is one step closer to clinching his fifth championship and cementing his status as a V8 Supercars great, but the dream is all over for Mark Winterbottom.

Whincup cruised his Holden to victory in a dramatic opening race of the Sydney 500 on Saturday, his first at the brutal street circuit in its four-year history.

The win extended his standings lead to 110 points over Red Bull teammate Craig Lowndes, who crawled home in 15th after sustaining damage in a bruising battle with long-time rival Winterbottom at Sydney Olympic Park.

While Lowndes remains in the hunt for this year’s crown – to be decided in the season’s final race on Sunday – a crash with 12 laps to go ended Winterbottom’s hope of claiming his first title .

The Ford man was among five drivers who failed to finish the category’s inaugural twilight race, the concrete-lined course also proving too much for Scott Pye, Maro Engel, Tim Blanchard and Scott McLaughlin.

Whincup started from pole and, despite briefly losing the lead to Winterbottom and Jonathon Webb heading into turn one, survived four safety car intermissions to finish 1.79secs ahead of the Holdens of Webb in second and Shane Van Gisbergen in third.

Jason Bright and Will Davison rounded out the top five.

Until now, 30-year-old Whincup had never finished better than fifth in Sydney.

His maiden victory on Saturday put him on track for a fifth championship in six years to equal the number of titles of the late Ian Geoghegan, Dick Johnson and Mark Skaife.

But the defending champion isn’t ready to celebrate.

“While I’m rapt with the win, I just want to keep it under wraps,” Whincup said.

“The championship’s well and truly still alive – although I’m in a slightly better position than I came here with.

“But tomorrow it’s going to be on and I just have to be focused.”

The final race of the year starts at 3.05pm (AEDT) on Sunday.