| Date | Overall winner(s) | Entrant | Car | Distance/Duration | Race title | Report |
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| SCCA National Sports Car Championship |
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| 1955 | Phil Hill | George E. Tilp | Ferrari 750 Monza | 150 miles (240 km) | Elkhart Lake's Road America Road Race | report |
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| 1956 | John Kilborn
Howard Hively | John Kilborn | Ferrari 375 MM | 6 hours | Road America 6 Hours | report |
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| 1957 | Phil Hill | Gene Greenspun | Ferrari 315 S | 500 miles (800 km) | Road America 500 | report |
|---|
| 1958 | Gaston Andrey
Lance Reventlow | North American Racing Team | Ferrari 335 S | 500 miles (800 km) | Road America 500 | report |
|---|
| 1959 | Ed Crawford
Walt Hansgen | Briggs Cunningham | Lister -Jaguar | 500 miles (800 km) | Road America 500 | report |
|---|
| 1960 | Dave Causey
Luke Stear | Dave Causey | Maserati Tipo 61 | 500 miles (800 km) | Road America 500 | report |
|---|
| 1961 | Walt Hansgen
Augie Pabst | Briggs Cunningham | Maserati Tipo 63 | 500 miles (800 km) | Road America 500 | report |
|---|
| 1962 | Jim Hall
Hap Sharp | Jim Hall | Chaparral 1-Chevrolet | 500 miles (800 km) | Road America 500 | report |
|---|
| United States Road Racing Championship |
|---|
| 1963 | Augie Pabst
Bill Wuesthoff | Porsche Car Import/Oliver Schmidt | Elva Mk.7-Porsche | 500 miles (800 km) | Road America 500 | report |
|---|
| 1964 | Walt Hansgen
Augie Pabst | John Mecom Jr. | Ferrari 250 LM | 500 miles (800 km) | Road America 500 | report |
|---|
| 1965 | Jim Hall
Hap Sharp
Ronnie Hissom | Jim Hall | Chaparral 2A-Chevrolet | 500 miles (800 km) | Road America 500 | report |
|---|
| 1966 | Chuck Parsons | Randy Hilton | McLarenElva Mk.II-Chevrolet | 500 miles (800 km) | Road America 500 | report |
|---|
| 1967 | Chuck Parsons
Skip Scott | Carl Haas | McLarenElva Mk.III-Chevrolet | 500 miles (800 km) | Road America 500 | report |
|---|
| 1968 | Chuck Parsons
Skip Scott | Carl Haas | Lola T70 Mk.3-Chevrolet | 500 miles (800 km) | Road America 500 | report |
|---|
| 1969–1978:Not held |
| IMSA GT Championship |
|---|
| 1979 | David Hobbs
Derek Bell | McLaren North America | BMW 320i Turbo | 500 miles (800 km) | Pabst 500 | report |
|---|
| 1980 | John Paul Jr.
John Paul, Sr. | JLP Racing | Porsche 935 JLP-2 | 500 miles (800 km) | Pabst 500 | report |
|---|
| 1981 | Rolf Stommelen
Harald Grohs | Andial Meister Racing | Porsche 935 K3 | 500 miles (800 km) | Pabst 500 | report |
|---|
| 1982 | John Fitzpatrick
David Hobbs | John Fitzpatrick Racing | Porsche 935 K4 | 500 miles (800 km) | Pabst 500 | report |
|---|
| 1983 | Klaus Ludwig
Tim Coconis | Zakspeed | Ford Mustang GTP | 460 miles (740 km)A | Pabst 500 | report |
|---|
| 1984 | Al Holbert
Derek Bell | Holbert Racing | Porsche 962 | 500 miles (800 km) | Budweiser 500 | report |
|---|
| 1985 | Drake Olson
Bobby Rahal | Dyson Racing | Porsche 962 | 500 miles (800 km) | Löwenbräu Classic | report |
|---|
| 1986 | Al Holbert
Al Unser Jr. | Holbert Racing | Porsche 962 | 500 miles (800 km) | Löwenbräu Classic | report |
|---|
| 1987 | Price Cobb
Johnny Dumfries | Dyson Racing | Porsche 962 | 500 miles (800 km) | Löwenbräu Classic | report |
|---|
| 1988 | Geoff Brabham
John Morton | Electramotive Engineering | Nissan GTP ZX-T | 500 km (310 mi) | Miller High Life 500 | report |
|---|
| 1989 | Geoff Brabham
Chip Robinson | Electramotive Engineering | Nissan GTP ZX-T | 500 km (310 mi) | Miller High Life 500 | report |
|---|
| 1990 | Geoff Brabham | Nissan Performance | Nissan NPT-90 | 250 km (160 mi)B | Chicago Tribune presents theNissan Grand Prix of Road America | report |
|---|
| 1991 | Davy Jones | Bud Light/Jaguar Racing | Jaguar XJR-16 | 300 km (190 mi)C | Nissan Grand Prix of Road America | report |
|---|
| 1992 | Juan Manuel Fangio II | All American Racers | Eagle Mk IIIToyota | 2 hours | Nissan Grand Prix of Road America | report |
|---|
| 1993 | John Winter
Manuel Reuter | Joest Porsche Racing | Porsche 962C | 500 km (310 mi) | Piggly Wiggly Grand Prix 500 Kilometers | report |
|---|
| 1994–1999Not held |
| Grand American Road Racing Championship |
|---|
| 2000 | Didier Theys
Fredy Lienhard
Mauro Baldi | Doran Lista Racing | Ferrari 333 SP-Judd | 500 miles (800 km) | Sargento Road America 500 | report |
|---|
| 2001 | Didier Theys
Fredy Lienhard
Mauro Baldi | Lista Doran Racing | Ferrari 333 SP-Judd | 500 miles (800 km) | Sargento Road America 500 | report |
|---|
| American Le Mans Series |
|---|
| 2002 | Tom Kristensen
Rinaldo Capello | Audi Sport North America | Audi R8 | 4 hours, 15 minutes | Road America 500 presented by theChicago Tribune | report |
|---|
| 2003 | Johnny Herbert
JJ Lehto | ADTChampion Racing | Audi R8 | 2 hours, 45 minutes | Road America 500 presented by theChicago Tribune | report |
|---|
| 2004 | JJ Lehto
Marco Werner | ADTChampion Racing | Audi R8 | 2 hours, 45 minutes | Road America 500 presented by theChicago Tribune | report |
|---|
| 2005 | Frank Biela
Emanuele Pirro | ADTChampion Racing | Audi R8 | 2 hours, 45 minutes | Generac 500 | report |
|---|
| 2006 | Frank Biela
Emanuele Pirro | Audi Sport North America | Audi R10 TDI | 2 hours, 45 minutes | Generac 500 | report |
|---|
| 2007 | Romain Dumas
Timo Bernhard | Penske Racing | Porsche RS Spyder | 4 hours | Generac 500 | report |
|---|
| 2008 | Lucas Luhr
Marco Werner | Audi Sport North America | Audi R10 TDI | 4 hours | Generac 500 | report |
|---|
| 2009 | Scott Sharp
David Brabham | PatrónHighcroft Racing | Acura ARX-02a | 2 hours, 45 minutes | Time Warner Cable Road Race Showcase | report |
|---|
| 2010 | Paul Drayson
Jonny Cocker | Drayson Racing | Lola B09/60 | 2 hours, 45 minutes | American Le Mans Series powered by eStar | report |
|---|
| 2011 | Klaus Graf
Lucas Luhr | Muscle MilkAston Martin Racing | Lola-Aston Martin B08/62 | 4 hours | Time Warner Cable Road Race Showcase | report |
|---|
| 2012 | Chris Dyson
Guy Smith | Dyson Racing | Lola B12/60MazdaMZR-R | 4 hours | Road America Road Race Showcase | report[1] |
|---|
| 2013 | Klaus Graf
Lucas Luhr | Muscle Milk Pickett Racing | HPD ARX-03cHonda | 2 hours, 45 minutes | Orion Energy Systems 245 | report[2] |
|---|
| IMSA SportsCar Championship |
|---|
| 2014 | João Barbosa
Christian Fittipaldi | Action Express Racing | CoyoteCorvette DPChevrolet | 2 hours, 45 minutes | Continental Tire Road Race Showcase | report[3] |
|---|
| 2015 | Dane Cameron
Eric Curran | Action Express Racing | CoyoteCorvette DPChevrolet | 2 hours, 40 minutes | Continental Tire Road Race Showcase | report |
|---|
| 2016 | Dane Cameron
Eric Curran | Action Express Racing | CoyoteCorvette DPChevrolet | 2 hours, 40 minutes | Continental Tire Road Race Showcase | report |
|---|
| 2017 | Pipo Derani
Johannes van Overbeek | Tequila Patrón ESM | Nissan Onroak DPi | 2 hours, 40 minutes | Continental Tire Road Race Showcase | report |
|---|
| 2018 | Jon Bennett
Colin Braun | CORE Autosport | Oreca 07 | 2 hours, 40 minutes | Continental Tire Road Race Showcase | report[4] |
|---|
| 2019 | Jonathan Bomarito
Harry Tincknell | Joest Racing | Mazda RT24-P | 2 hours, 40 minutes | Road Race Showcase at Road America | Report |
|---|
| 2020 | Hélio Castroneves
Ricky Taylor | Team Penske | Acura ARX-05 | 2 hours, 40 minutes | IMSA SportsCar Weekend | Report |
|---|
| 2021 | Pipo Derani
Felipe Nasr | Action Express Racing | Cadillac DPi-V.R | 2 hours, 40 minutes | IMSA SportsCar Weekend | Report |
|---|
| 2022 | Filipe Albuquerque
Ricky Taylor | WTR - Konica Minolta Acura | Acura ARX-05 | 2 hours, 40 minutes | IMSA Fastlane SportsCar Weekend | report |
|---|
| 2023 | Matt Campbell
Felipe Nasr | Porsche Penske Motorsport | Porsche 963 | 2 hours, 40 minutes | IMSA SportsCar Weekend | report |
|---|
| 2024 | Nick Tandy
Mathieu Jaminet | Porsche Penske Motorsport | Porsche 963 | 2 hours, 40 minutes | IMSA SportsCar Weekend | report |
|---|
| 2025 | Philipp Eng
Dries Vanthoor | BMW M Team RLL | BMW M Hybrid V8 | 2 hours, 40 minutes | Motul SportsCar Grand Prix | report |
|---|