In more than a century of racing at the Indianapolis Motor Speedway (IMS) only three men -- A.J. Foyt, Al Unser Sr. and Rick Mears -- have won the 500 four times and with a win on Sunday Castroneves would become the first non-American to join that group.
Now on the downside of his career, the 44-year-old no longer drives full-time on the IndyCar Series but Roger Penske continues to give his long-time employee a competitive car and a chance to get his name on the Borg-Warner trophy again.
The bubbly Brazilian has always been a driver to take motivation from wherever he can find it and this week is drawing inspiration from Woods, who completed one of sport's all-time great comebacks last month when he ended an 11-year major title drought with a stunning victory at the Masters.
"You know it took Tiger Woods 10 years to go back and win another big one so maybe it could be this year (for me)," said Castroneves. "You're always looking for positive ways to look and I'm always a positive guy and realistic at the same time.
"I can only imagine how special it would be. At this point you can dream big but you still have to execute first."
Castroneves was quick to put his mark on the Indy 500, winning on his Brickyard debut in 2001 and repeating in 2002.
It was seven years before he returned to Victory Lane in 2009 and he has not found his way back since, though he has twice come agonisingly close, finishing as runner-up in 2014 and 2017.
In 2014 Ryan Hunter-Reay denied Castroneves victory by 0.0600 seconds, the second-closest finish in race history.
Castroneves said it was the memory of 2017 that haunted him most, recalling how Japan's Takuma Sato powered past him with five laps remaining then bravely fought off the Brazilian to take the checkered flag.
"It’s hard to forget the ones you’ve missed," said Castroneves, who has looked right at home back in his Penzoil Team Penske Chevrolet, qualifying 12th fastest in the 33-car field.
"Obviously great memories of the ones that happened but the ones you’ve missed stay in your mind.
"I mean 2017 with Takuma was really tough; I did everything I could but he did a really great job.
"Hopefully I don't have to think this year about being a close call and just make it happen."
(Editing by Clare Fallon)
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