Sponsored by Miller 1977-1995
Sponsored by Coor's 1996-2002
Sponsored by Checkers/Rally's: 2003-2007
Sponsored by McDonald's: 2008
Unsponsored: 2009
Sponsored by IZOD: 2010-2011
| Year | Team | Driver | Crew Chief | Time |
| 1977 | Carillo | Jim McElreath | Dave Klymm | 15.09 |
| 1978 | Team McLaren | Johnny Rutherford | Steve Roby | 13.80 |
| 1979 | Team McLaren | Johnny Rutherford | Steve Roby | 13.51 |
| 1980 | Sherman Armstong | Tom Bigelow | Paul Leffler | 14.04 |
| 1981 | Penske Racing | Bobby Unser | Laurie Gerrish | 13.00 |
| 1982 | Penske Racing | Rick Mears | Peter Parrott | 13.93 |
| 1983 | Penske Racing | Rick Mears | Peter Parrott | 13.86 |
| 1984 | Kraco Racing | Michael Andretti | Haf Haffendum | 18.52 |
| 1985 | Penske Racing | Danny Sullivan | Chuck Sprague | 11.74 |
| 1986 | Penske Racing | Danny Sullivan | Chuck Sprague | 20.29 |
| 1987 | Newman-Haas Racing | Mario Andretti | Colin Duff | 18.05 |
| 1988 | Penske Racing | Danny Sullivan | Chuck Sprague | 14.78 |
| 1989 | Galles Racing | Al Unser, Jr. | Owen Snyder | 14.71 |
| 1990 | Galles-Kraco Racing | Al Unser, Jr. | Owen Snyder | 14.09 |
| 1991 | Patrick Racing | Danny Sullivan | Mike Hull | 13.11 |
| 1992 | Rahal-Hogan Racing | Bobby Rahal | Jim Prescott | 13.32 |
| 1993 | Galles-Kraco Racing | Al Unser, Jr. | Owen Synder | 13.11 |
| 1994 | Forsythe/Green Racing | Jacques Villeneuve | Kyle Moyer | 12.86 |
| 1995 | Team Green | Jacques Villeneuve | Kyle Moyer | 14.56 |
| 1996 | Galles Racing | Davy Jones | Mitch Davis | 14.18 |
| 1997 | Galles Racing | Kenny Brack | Gary Armentrout | 14.284 |
| 1998 | Panther Racing | Scott Goodyear | Kevin Blanch | 17.307 |
| 1999 | Galles Racing | Davey Hamilton | Darren Russell | 12.680 |
| 2000 | Panther Racing | Scott Goodyear | Kevin Blanch | 11.190 |
| 2001 | Kelley Racing | Scott Sharp | Robert Perez | 9.20 |
| 2002 | Marlboro Team Penske | Helio Castroneves | Rick Rinaman | 8.5555 |
| 2003 | Red Bull Cheever Racing | Buddy Rice | Dave Meehan | 8.8401 |
| 2004 | Rahal-Letterman Racing | Buddy Rice | Ricardo Nault | 12.3365 |
| 2005 | Malboro Team Penske | Sam Hornish, Jr. | Matt Jonsson | 8.9704 |
| 2006 | Malboro Team Penske | Helio Castroneves | Rick Rinaman | 8.08524 |
| 2007 | Team Penske | Helio Castroneves | Rick Rinaman | 8.355 |
| 2008 | Event cancelled due to rain | |||
| 2009 | Team Penske | Helio Castroneves | Rick Rinaman | 7.962 |
| 2010 | Team Penske | Helio Castroneves | Sean Hanrahan | 8.001 |
| 2011 | Team Penske | Ryan Briscoe | Matt Jonsson | 7.882 |
The annual Pit Stop Challenge is held a couple days before the race, on Carb Day. Teams qualify from their positions on the grid, and from the top teams in IndyCar Series competition. As many as tweleve teams compete in a single-elimination, tournament-style (bracket) competition, two cars at a time. Pit crews must change four tires and hook-up the fuel hose to simulate refueling. The driver actually drives the car in to a special pit box, and the time is taken from the entry into the box to the exit. Winners are based on total time, not necessarily first out out the pit box. Penalties can be added for loose lug nuts, and other infractions.
Starting in 2005, Carb Day was moved from Thursday to the Friday before the Indy 500. In 2008, rain fell just 12 minutes into the Carb Day practice, and washed out all other events for the day. Rather than rescheduling the Pit Stop Contest, it was cancelled outright for the year. A few weeks later, the $100,000 prize money set aside for the event was donated to Belle Isle Park and Hole in the Wall Camps.