| May 26, 1946 | Winchester Speedway, Winchester, IN | AAA Sprint Car | Bus Wilbert | |
| June 9, 1946 | Winchester Speedway, Winchester, IN | AAA Sprint Car | Bus Wilbert | |
| August 11, 1946 | Winchester Speedway, Winchester, IN | AAA Sprint Car | Elbert Booker | |
| September 1, 1946 | Winchester Speedway, Winchester, IN | AAA Sprint Car | Charles Van Acker | |
| April 27, 1947 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Duke Dinsmore | |
| May 25, 1947 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Carl Scarborough | |
| September 21, 1947 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Spider Webb | |
| May 2, 1948 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Spider Webb | |
| May 30, 1948 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Spider Webb | |
| July 25, 1948 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Ted Horn | |
| July 30, 1950 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Duane Carter | |
| October 15, 1950 | Winchester Speedway, Winchester, IN | NASCAR Grand National | Lloyd Moore | |
| May 6, 1951 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Jimmy Daywalt | |
| June 29, 1952 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Troy Ruttman | |
| May 3, 1953 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Pat O'Connor | |
| May 31, 1953 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Pat O'Connor | |
| July 12, 1953 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Pat O'Connor | |
| August 9, 1953 | Winchester Speedway, Winchester, IN | AAA Stock Car | Marshall Teague | |
| September 27, 1953 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Mike Nazaruk | |
| May 2, 1954 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Mike Nazaruk | |
| May 23, 1954 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Johnny Key | |
| May 30, 1954 | Winchester Speedway, Winchester, IN | AAA Sprint Car (Midwest) | Bob King | |
| May 20, 1956 | Winchester Speedway, Winchester, IN | USAC Sprint Car (Midwest) | Elmer George | |
| July 1, 1956 | Winchester Speedway, Winchester, IN | USAC Sprint Car (Midwest) | Eddie Sachs | |
| September 9, 1956 | Winchester Speedway, Winchester, IN | USAC Sprint Car (Midwest) | Eddie Sachs | |
| May 5, 1957 | Winchester Speedway, Winchester, IN | USAC Sprint Car (Midwest) | Andy Linden | |
| June 30, 1957 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Don O'Dell | |
| September 15, 1957 | Winchester Speedway, Winchester, IN | USAC Sprint Car (Midwest) | Elmer George | |
| July 13, 1958 | Winchester Speedway, Winchester, IN | USAC Sprint Car (Midwest) | Don Branson | |
| September 14, 1958 | Winchester Speedway, Winchester, IN | USAC Midget | Don Branson | |
| May 29, 1960 | Winchester Speedway, Winchester, IN | Sprint Car | Parnelli Jones | |
| September 2, 1962 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Roger McCluskey | |
| July 12, 1964 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Bud Tinglestad | |
| August 30, 1964 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Jack Bowsher | |
| September 6, 1964 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Gordon Johncock | |
| May 30, 1965 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Jud Larson | |
| July 11, 1965 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Johnny Rutherford | |
| October 10, 1965 | Pepsi Cola 100 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Johnny Rutherford |
| May 29, 1966 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Jud Larson | |
| July 10, 1966 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Roger McCluskey | |
| September 18, 1966 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Al Smith | |
| April 30, 1967 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Jerry Daniels | |
| May 28, 1967 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Bob Wente | |
| September 17, 1967 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Sam Sessions | |
| May 5, 1968 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Larry Dickson | |
| September 15, 1968 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Larry Dickson | |
| September 14, 1969 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Gary Bettenhausen | |
| October 4, 1970 | Dri-Power 400 | Winchester Speedway, Winchester, IN | ASA Late Model Stock Car | Dave Sorg |
| June 27, 1971 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Larry Dickson | |
| October 4, 1971 | Dri-Power 400 | Winchester Speedway, Winchester, IN | ASA Late Model Stock Car | Dennis Miles |
| April 30, 1972 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Ralph Latham | |
| June 25, 1972 | Winchester 100 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Bobby Watson |
| October 1, 1972 | Dri-Power 400 | Winchester Speedway, Winchester, IN | Stock Car | Dave Sorg |
| May 6, 1973 | Winchester Speedway, Winchester, IN | ASA Stock Car | Jack Shanklin | |
| July 15, 1973 | Liberty Bell 150 | Winchester Speedway, Winchester, IN | ASA Stock Car | Dick Freeman |
| September 3, 1973 | Labor Day 100 | Winchester Speedway, Winchester, IN | ASA Stock Car | John Vallo |
| September 30, 1973 | Dri-Power 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Vern Schrock |
| April 7, 1974 | Winchester Speedway, Winchester, IN | ASA Stock Car | Shorty Hinshaw | |
| August 11, 1974 | Liberty Bell 100 | Winchester Speedway, Winchester, IN | ASA Stock Car | Dennis Miles |
| September 8, 1974 | Labor Day 100 | Winchester Speedway, Winchester, IN | ASA Stock Car | John Vallo |
| September 29, 1974 | Dri-Powr 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker |
| April 13, 1975 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker | |
| May 26, 1975 | Carling 100 | Winchester Speedway, Winchester, IN | ASA Stock Car | John Vallo |
| June 22, 1975 | Winchester Speedway, Winchester, IN | ASA Stock Car | Rodney Combs | |
| July 4, 1975 | Liberty Bell 100 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker |
| September 1, 1975 | Labor Day 100 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker |
| September 28, 1975 | Dri-Powr 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker |
| April 18, 1976 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker | |
| April 18, 1976 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker | |
| May 31, 1976 | Memorial 200 | Winchester Speedway, Winchester, IN | ASA Stock Car | Larry Phillips |
| July 5, 1976 | Winchester Speedway, Winchester, IN | ASA Stock Car | John Anderson | |
| September 6, 1976 | Labor Day 100 | Winchester Speedway, Winchester, IN | ASA Stock Car | Rodney Combs |
| October 3, 1976 | Dri-Powr 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker |
| April 17, 1977 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker | |
| April 17, 1977 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker | |
| May 30, 1977 | Memorial 200 | Winchester Speedway, Winchester, IN | ASA Stock Car | Dave Watson |
| May 30, 1977 | Memorial 200 | Winchester Speedway, Winchester, IN | ASA Stock Car | Rich Knotts |
| July 4, 1977 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker | |
| September 5, 1977 | Flagship 100 | Winchester Speedway, Winchester, IN | ASA Stock Car | Randy Sweet |
| October 2, 1977 | Dri-Power 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker |
| April 29, 1978 | Winchester 100 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker |
| May 29, 1978 | Memorial Day 200 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker |
| October 1, 1978 | Dri-Powr 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker |
| April 15, 1979 | Champion Motor Home 100 | Winchester Speedway, Winchester, IN | ASA Stock Car | Mark Martin |
| October 7, 1979 | Dri-Power 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Don Gregory |
| May 26, 1980 | Memorial 200 | Winchester Speedway, Winchester, IN | ASA Stock Car | Mark Martin |
| October 5, 1980 | Dri-Power 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Terry Senneker |
| May 17, 1981 | Memorial 100 | Winchester Speedway, Winchester, IN | ASA Late Model Sportsman | Glenn Ohlmann |
| May 17, 1981 | Memorial 200 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker |
| May 25, 1981 | Winchester Speedway, Winchester, IN | USAC Stock Car | Scott Stovall | |
| May 25, 1981 | Winchester Speedway, Winchester, IN | USAC Midget | Mel Kenyon | |
| July 26, 1981 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Rich Vogler | |
| October 4, 1981 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Mike Eddy |
| June 13, 1982 | Amsoil 200 | Winchester Speedway, Winchester, IN | ASA Stock Car | Dick Trickle |
| July 5, 1982 | Winchester 100 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Marvin Smith |
| October 3, 1982 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Rusty Wallace |
| July 3, 1983 | Winchester 100 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Marvin Smith |
| October 2, 1983 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Mike Eddy |
| July 1, 1984 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker | |
| September 30, 1984 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker |
| June 30, 1985 | Carquest 100 | Winchester Speedway, Winchester, IN | ASA Gran Marque | Mike Eddy |
| September 28, 1985 | Carquest 100 | Winchester Speedway, Winchester, IN | ASA Gran Marque | Mark Martin |
| September 29, 1985 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Mark Martin |
| October 5, 1986 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Mark Martin |
| October 4, 1987 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Butch Miller |
| June 25, 1988 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Tracy Leslie | |
| October 2, 1988 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Ted Musgrave |
| October 1, 1989 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Butch Miller |
| September 15, 1990 | Winchester ARCA 125 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Bob Keselowski |
| September 30, 1990 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Bob Senneker |
| October 6, 1991 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Glenn Allen Jr. |
| October 4, 1992 | Featherlite Trailers Winchester 400 | Winchester Speedway, Winchester, IN | NASCAR All Pro Series | Tim Steele |
| October 2, 1993 | Winchester 150 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Tim Steele |
| October 3, 1993 | Featherlite Trailers Winchester 400 | Winchester Speedway, Winchester, IN | NASCAR All Pro Series | Mike Cope |
| October 1, 1994 | Winchester 150 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Gary Bradberry |
| October 2, 1994 | Featherlite Trailers Winchester 400 | Winchester Speedway, Winchester, IN | NASCAR All Pro Series | Mike Cope |
| April 2, 1995 | Winchester Speedway, Winchester, IN | USAC Midget | Mike Bliss | |
| April 2, 1995 | Rich Vogler Classic | Winchester Speedway, Winchester, IN | USAC Sprint Car | Kenny Irwin |
| June 24, 1995 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Tray House | |
| July 6, 1995 | Hoosier Festival of Speed | Winchester Speedway, Winchester, IN | USAC Midget | Brian Gerster |
| July 15, 1995 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Eric Gordon | |
| August 10, 1995 | Winchester Speedway, Winchester, IN | USAC Sprint Car | Chet Fillip | |
| September 30, 1995 | ARCA 150 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Tim Steele |
| October 1, 1995 | Winchester 400 | Winchester Speedway, Winchester, IN | NASCAR All Pro Series | Mike Cope |
| October 22, 1995 | Sam Sessions Memorial | Winchester Speedway, Winchester, IN | USAC Midget | Doug Kalitta |
| October 22, 1995 | Sam Sessions Memorial | Winchester Speedway, Winchester, IN | USAC Sprint Car | Doug Kalitta |
| September 28, 1996 | Roger Holdeman Memorial 150 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Frank Kimmel |
| September 29, 1996 | Winchester 400 | Winchester Speedway, Winchester, IN | NASCAR All Pro Series | Scot Walters |
| September 27, 1997 | Roger Holdeman Memorial 150 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Tim Steele |
| September 28, 1997 | Winchester 400 | Winchester Speedway, Winchester, IN | NASCAR All Pro Series | Hank Parker Jr. |
| September 26, 1998 | Snap-On Tools 150 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Bob Strait |
| September 27, 1998 | Winchester 400 | Winchester Speedway, Winchester, IN | NASCAR All Pro Series | Derrick Gilchrist |
| June 6, 1999 | Winchester Speedway, Winchester, IN | USAC Midget | Ryan Newman | |
| July 2, 1999 | Winchester Speedway, Winchester, IN | NAMARS Midget | Sarah Fisher | |
| July 30, 1999 | Roger Holdeman Memorial | Winchester Speedway, Winchester, IN | NAMARS Midget | Dan Drinan |
| August 29, 1999 | Winchester ARCA 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Tracy Leslie |
| September 26, 1999 | Winchester 400 | Winchester Speedway, Winchester, IN | CRA Kendall Late Model | Brian Ross |
| October 24, 1999 | Sammy Sessions Memorial | Winchester Speedway, Winchester, IN | USAC Midget | Ryan Newman |
| August 12, 2000 | Astral Carrier ARCA 250 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Frank Kimmel |
| October 1, 2000 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Gary St. Amant |
| April 22, 2001 | ARCA Re/Max 250 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Tim Steele |
| July 28, 2001 | Lucas Oil 250 | Winchester Speedway, Winchester, IN | USAR Pro Cup Northern | Donnie Hill |
| September 23, 2001 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Joey Clanton |
| May 5, 2002 | Naturally Fresh Dressings 250 | Winchester Speedway, Winchester, IN | USAR Pro Cup Northern | Brian Ross |
| August 31, 2002 | GoldenPalace.com 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Frank Kimmel |
| September 22, 2002 | Alan Kulwicki Memorial | Winchester Speedway, Winchester, IN | USAR Pro Cup | Clay Rogers |
| October 6, 2002 | Winchester 400 | Winchester Speedway, Winchester, IN | ASA Stock Car | Gary St. Amant |
| August 30, 2003 | Winchester RE/MAX 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Frank Kimmel |
| August 14, 2005 | Lincoln Welders 50 | Winchester Speedway, Winchester, IN | ARCA Lincoln Welders Truck | Brett Rowe |
| May 7, 2006 | ARCA 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Frank Kimmel |
| August 13, 2006 | Lincoln Welders 50 | Winchester Speedway, Winchester, IN | ARCA Lincoln Welders Truck | Danny Jackson |
| May 6, 2007 | Winchester ARCA 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Billy Leslie |
| May 23, 2010 | King of the Wings | Winchester Speedway, Winchester, IN | Must See/HOSS Sprint Car | Dave Steele |
| August 22, 2010 | Rich Vogler Classic | Winchester Speedway, Winchester, IN | USAC Sprint Car | Shane Hmiel |
| June 25, 2011 | Winchester 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Dakoda Armstrong |
| August 21, 2011 | Winged Sprint Extravaganza | Winchester Speedway, Winchester, IN | Must See Racing Sprint Car | Jason Blonde |
| September 18, 2011 | Rich Vogler Classic | Winchester Speedway, Winchester, IN | USAC Pavement Sprint Car | Tracy Hines |
| May 20, 2012 | Xtreme Speed Challenge | Winchester Speedway, Winchester, IN | Must See Racing Sprint Car | Troy DeCaire |
| May 20, 2012 | Xtreme Speed Challenge | Winchester Speedway, Winchester, IN | Must See Racing Supermodified | Jim Paller |
| June 24, 2012 | Herr's Chase the Taste 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Alex Bowman |
| August 19, 2012 | King of the Wings | Winchester Speedway, Winchester, IN | Must See Racing Sprint Car | Troy DeCaire |
| May 19, 2013 | Xtreme Speed Challenge | Winchester Speedway, Winchester, IN | Must See Racing Sprint Car | JoJo Helberg |
| May 19, 2013 | Xtreme Speed Challenge | Winchester Speedway, Winchester, IN | Must See Racing Supermodified | Dave McKnight |
| June 29, 2013 | Winchester 100 | Winchester Speedway, Winchester, IN | ARCA CRA All-Stars | Travis Braden |
| June 30, 2013 | Herr's Chase the Taste 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Frank Kimmel |
| August 18, 2013 | King of the Wings | Winchester Speedway, Winchester, IN | Must See Racing Sprint Car | Brian Gerster |
| September 1, 2013 | Winchester 100 | Winchester Speedway, Winchester, IN | ARCA CRA All-Stars | Trent Snyder |
| September 2, 2013 | Winchester 100 | Winchester Speedway, Winchester, IN | ARCA CRA Super Series | Johnny Van Doorn |
| July 4, 2014 | King of the Wing | Winchester Speedway, Winchester, IN | AVSS Sprint Car | JoJo Helberg |
| July 6, 2014 | Herr's Chase the Taste 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Brandon Jones |
| June 28, 2015 | Herr's Chase The Taste 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Austin Self |
| June 26, 2016 | Herr's Potato Chips 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Chase Briscoe |
| August 6, 2017 | Winchester 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Kyle Benjamin |
| September 19, 2020 | Toyota 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Ty Gibbs |
| July 31, 2021 | Calypso Lemonade 200 | Winchester Speedway, Winchester, IN | ARCA Stock Car | Ty Gibbs |