| Year | Date | Opponent | Us | Them | Result | W | L | T | OT | Where | Location | Field | Coach | Notes | |
| 1903 | Wooster | 6 | 22 | L | 1 | ||||||||||
| 1913 | 10/10 | Wooster | 0 | 67 | L | 1 | Home | Orrville | Borden Field | Livingston Goodman | |||||
| 1913 | 11/7 | Wooster | 0 | 55 | L | 1 | Away | Wooster | Livingston Goodman | ||||||
| 1914 | 9/25 | Wooster | 0 | 55 | L | 1 | Away | Wooster | Walter Chilcott | ||||||
| 1914 | 10/16 | Wooster | 0 | 20 | L | 1 | Home | Orrville | Graber Park | Walter Chilcott | |||||
| 1915 | 10/1 | Wooster | 0 | 7 | L | 1 | Home | Orrville | Borden Field | M. C. Avery | |||||
| 1916 | 11/3 | Wooster | 0 | 20 | L | 1 | Away | Wooster | Retzler | ||||||
| 1917 | 10/13 | Wooster | 13 | 0 | W | 1 | Home | Orrville | Borden Field | Retzler | |||||
| 1918 | Wooster | 7 | 43 | L | 1 | E. R. Wise | |||||||||
| 1919 | 11/22 | Wooster | 7 | 13 | L | 1 | Home | Orrville | Borden Field | E. R. Wise | |||||
| 1920 | Wooster | 7 | 0 | W | 1 | Away | Wooster | Severance Stadium | John Lindsay | ||||||
| 1921 | 9/30 | Wooster | 13 | 0 | W | 1 | Home | Orrville | John Lindsay | ||||||
| 1922 | 10/14 | Wooster | 2 | 27 | L | 1 | Away | Wooster | Severance Stadium | Homer Torreyson | |||||
| 1923 | 11/29 | Wooster | 0 | 13 | L | 1 | Home | Orrville | Cate Field | Joe Hermann | |||||
| 1924 | 11/27 | Wooster | 7 | 7 | T | 1 | Away | Wooster | Severance Stadium | Joe Hermann | |||||
| 1925 | 11/26 | Wooster | 0 | 6 | L | 1 | Home | Orrville | Charles Pugh | ||||||
| 1926 | 10/30 | Wooster | 34 | 0 | W | 1 | Away | Wooster | Ken Mills | ||||||
| 1927 | 9/24 | Wooster | 0 | 0 | T | 1 | Away | Wooster | Richard White | ||||||
| 1927 | 10/29 | Wooster | 20 | 13 | W | 1 | Home | Orrville | Sanderson Field | Richard White | |||||
| 1928 | 11/16 | Wooster | 0 | 19 | L | 1 | Away | Wooster | Richard White | ||||||
| 1929 | 10/26 | Wooster | 12 | 12 | T | 1 | Home | Orrville | Richard White | ||||||
| 1930 | 10/25 | Wooster | 0 | 61 | L | 1 | Away | Wooster | Richard White | ||||||
| 1931 | 10/24 | Wooster | 0 | 61 | L | 1 | Home | Orrville | Richard White | ||||||
| 1932 | 10/21 | Wooster | 0 | 26 | L | 1 | Away | Wooster | Elmer Reger | ||||||
| 1933 | 10/21 | Wooster | 6 | 19 | L | 1 | Home | Orrville | Elmer Reger | ||||||
| 1934 | 10/19 | Wooster | 13 | 8 | W | 1 | Away | Wooster | Elmer Reger | ||||||
| 1935 | 10/19 | Wooster | 7 | 6 | W | 1 | Home | Orrville | Al Tanner | ||||||
| 1936 | 10/24 | Wooster | 0 | 13 | L | 1 | Away | Wooster | Fairgrounds | Al Tanner | |||||
| 1937 | 11/11 | Wooster | 0 | 12 | L | 1 | Home | Orrville | Harry Strobel | ||||||
| 1938 | 11/11 | Wooster | 0 | 6 | L | 1 | Away | Wooster | Fairgrounds | Harry Strobel | |||||
| 1939 | 11/10 | Wooster | 0 | 0 | T | 1 | Home | Orrville | Harry Strobel | ||||||
| 1940 | 11/11 | Wooster | 13 | 7 | W | 1 | Away | Wooster | Harry Strobel | ||||||
| 1941 | 11/11 | Wooster | 0 | 33 | L | 1 | Home | Orrville | Harry Strobel | ||||||
| 1942 | 11/11 | Wooster | 0 | 34 | L | 1 | Away | Wooster | Maurer Field | Jack McLaughlin | |||||
| 1943 | 11/10 | Wooster | 0 | 31 | L | 1 | Home | Orrville | Marshall McCuen | ||||||
| 1944 | 11/11 | Wooster | 13 | 13 | T | 1 | Away | Wooster | Maurer Field | Marshall McCuen | |||||
| 1945 | 11/9 | Wooster | 30 | 0 | W | 1 | Home | Orrville | Marshall McCuen | ||||||
| 1946 | 11/11 | Wooster | 0 | 6 | L | 1 | Away | Wooster | Severance Stadium | Bill Coyer | |||||
| 1947 | 11/7 | Wooster | 31 | 6 | W | 1 | Home | Orrville | Bill Coyer | ||||||
| 1948 | 11/12 | Wooster | 12 | 38 | L | 1 | Away | Wooster | Maurer Field | Bill Coyer | |||||
| 1949 | 11/11 | Wooster | 0 | 41 | L | 1 | Home | Orrville | Bill Coyer | ||||||
| 1950 | 11/10 | Wooster | 0 | 53 | L | 1 | Away | Wooster | Maurer Field | Carl Stager | |||||
| 1951 | 11/9 | Wooster | 33 | 14 | W | 1 | Home | Orrville | Carl Stager | ||||||
| 1952 | 11/7 | Wooster | 6 | 21 | L | 1 | Away | Wooster | Maurer Field | Robert Gobin | |||||
| 1953 | 11/13 | Wooster | 12 | 6 | W | 1 | Home | Orrville | Robert Gobin | ||||||
| 1954 | 11/12 | Wooster | 12 | 13 | L | 1 | Away | Wooster | Maurer Field | Robert Gobin | |||||
| 1955 | 11/11 | Wooster | 0 | 41 | L | 1 | Home | Orrville | Bill Shunkwiler | ||||||
| 1956 | 11/9 | Wooster | 6 | 20 | L | 1 | Away | Wooster | Maurer Field | Bill Shunkwiler | |||||
| 1957 | 11/8 | Wooster | 0 | 6 | L | 1 | Home | Orrville | Bill Shunkwiler | ||||||
| 1958 | 11/7 | Wooster | 0 | 0 | T | 1 | Away | Wooster | Maurer Field | Bill Shunkwiler | |||||
| 1959 | 11/13 | Wooster | 32 | 22 | W | 1 | Home | Orrville | Red Rider Stadium | Bill Shunkwiler | |||||
| 1960 | 11/11 | Wooster | 12 | 16 | L | 1 | Away | Wooster | Maurer Field | Bill Shunkwiler | |||||
| 1961 | 11/10 | Wooster | 6 | 12 | L | 1 | Home | Orrville | Red Rider Stadium | Bill Shunkwiler | |||||
| 1962 | 10/9 | Wooster | 6 | 16 | L | 1 | Away | Wooster | Maurer Field | Bill Shunkwiler | |||||
| 1963 | 11/8 | Wooster | 20 | 12 | W | 1 | Home | Orrville | Red Rider Stadium | Bill Shunkwiler | |||||
| 1964 | 11/13 | Wooster | 40 | 8 | W | 1 | Away | Wooster | Maurer Field | Bill Shunkwiler | |||||
| 1965 | 11/12 | Wooster | 0 | 8 | L | 1 | Home | Orrville | Red Rider Stadium | Mo Tipton | |||||
| 1966 | 11/11 | Wooster | 0 | 0 | T | 1 | Away | Wooster | Maurer Field | Mo Tipton | |||||
| 1967 | 11/10 | Wooster | 6 | 20 | L | 1 | Home | Orrville | Red Rider Stadium | Mo Tipton | |||||
| 1968 | 11/8 | Wooster | 6 | 6 | T | 1 | Away | Wooster | Maurer Field | Mo Tipton | |||||
| 1969 | 11/7 | Wooster | 12 | 12 | T | 1 | Home | Orrville | Red Rider Stadium | Mo Tipton | |||||
| 1970 | 11/13 | Wooster | 6 | 7 | L | 1 | Away | Wooster | Maurer Field | Mo Tipton | |||||
| 1971 | 11/12 | Wooster | 6 | 14 | L | 1 | Home | Orrville | Red Rider Stadium | Mo Tipton | |||||
| 1972 | 11/10 | Wooster | 13 | 0 | W | 1 | Away | Wooster | Maurer Field | Mo Tipton | |||||
| 1973 | 11/9 | Wooster | 7 | 47 | L | 1 | Home | Orrville | Red Rider Stadium | Mo Tipton | |||||
| 1974 | 11/8 | Wooster | 17 | 34 | L | 1 | Away | Wooster | Maurer Field | Mo Tipton | |||||
| 1975 | 11/7 | Wooster | 42 | 7 | W | 1 | Home | Orrville | Red Rider Stadium | Mo Tipton | |||||
| 1976 | 11/12 | Wooster | 37 | 13 | W | 1 | Away | Wooster | Maurer Field | Mo Tipton | |||||
| 1977 | 11/11 | Wooster | 15 | 0 | W | 1 | Home | Orrville | Red Rider Stadium | Mo Tipton | |||||
| 1978 | 11/10 | Wooster | 7 | 6 | W | 1 | Away | Wooster | Maurer Field | Mo Tipton | |||||
| 1979 | 11/9 | Wooster | 0 | 3 | L | 1 | Home | Orrville | Red Rider Stadium | Mo Tipton | |||||
| 1981 | 11/6 | Wooster | 0 | 7 | L | 1 | Home | Orrville | Red Rider Stadium | Mo Tipton | |||||
| 1982 | 11/5 | Wooster | 26 | 6 | W | 1 | Away | Wooster | Maurer Field | Mo Tipton | |||||
| 1983 | 11/4 | Wooster | 23 | 21 | W | 1 | Home | Orrville | Red Rider Stadium | Mo Tipton | |||||
| 1984 | 11/2 | Wooster | 21 | 6 | W | 1 | Away | Wooster | Maurer Field | Mo Tipton | |||||
| 1985 | 11/1 | Wooster | 28 | 20 | W | 1 | Home | Orrville | Red Rider Stadium | Mo Tipton | |||||
| 1986 | 10/31 | Wooster | 6 | 10 | L | 1 | Away | Wooster | Maurer Field | Mo Tipton | |||||
| 1987 | 11/6 | Wooster | 21 | 10 | W | 1 | Home | Orrville | Red Rider Stadium | Mo Tipton | |||||
| 1988 | 11/4 | Wooster | 13 | 10 | W | 1 | Away | Wooster | Maurer Field | Bill McMillan | |||||
| 1989 | 10/27 | Wooster | 6 | 7 | L | 1 | Home | Orrville | Red Rider Stadium | Bill McMillan | |||||
| 1990 | 10/26 | Wooster | 33 | 6 | W | 1 | Away | Wooster | Maurer Field | Bill McMillan | |||||
| 1991 | 11/1 | Wooster | 24 | 23 | W | 1 | Home | Orrville | Red Rider Stadium | Bill McMillan | |||||
| 1992 | 11/6 | Wooster | 17 | 15 | W | 1 | Away | Wooster | Maurer Field | Bill McMillan | |||||
| 1993 | 11/5 | Wooster | 10 | 34 | L | 1 | Home | Orrville | Red Rider Stadium | Bill McMillan | |||||
| 1994 | 11/4 | Wooster | 40 | 0 | W | 1 | Away | Wooster | Maurer Field | Bill McMillan | |||||
| 1995 | 11/3 | Wooster | 55 | 6 | W | 1 | Home | Orrville | Red Rider Stadium | Bill McMillan | |||||
| 1996 | 11/1 | Wooster | 17 | 14 | W | 1 | Away | Wooster | Follis Field | Bill McMillan | |||||
| 1997 | 10/31 | Wooster | 34 | 22 | W | 1 | Home | Orrville | Red Rider Stadium | Bill McMillan | |||||
| 1998 | 11/6 | Wooster | 44 | 12 | W | 1 | Away | Wooster | Follis Field | Bill McMillan | |||||
| 1999 | 10/29 | Wooster | 42 | 0 | W | 1 | Home | Orrville | Red Rider Stadium | Bill McMillan | |||||
| 2000 | 10/27 | Wooster | 25 | 28 | L | 1 | Away | Wooster | Follis Field | Bill McMillan | |||||
| 2001 | 10/26 | Wooster | 6 | 23 | L | 1 | Home | Orrville | Red Rider Stadium | Bill McMillan | |||||
| 2002 | 10/25 | Wooster | 28 | 29 | L | 1 | Away | Wooster | Follis Field | Bill McMillan | |||||
| 2003 | 10/24 | Wooster | 27 | 41 | L | 1 | Home | Orrville | Red Rider Stadium | Bill McMillan | |||||
| 2004 | 10/29 | Wooster | 20 | 21 | L | 1 | Away | Wooster | Follis Field | Bill McMillan | |||||
| 2005 | 10/28 | Wooster | 21 | 14 | W | 1 | Home | Orrville | Red Rider Stadium | Bill McMillan | |||||
| 2006 | 10/27 | Wooster | 28 | 0 | W | 1 | Away | Wooster | Follis Field | Doug Davault | |||||
| 2007 | 10/26 | Wooster | 14 | 0 | W | 1 | Home | Orrville | Red Rider Stadium | Doug Davault | |||||
| 2008 | 10/24 | Wooster | 31 | 0 | W | 1 | Away | Wooster | Follis Field | Doug Davault | |||||
| 2009 | 10/30 | Wooster | 15 | 7 | W | 1 | Home | Orrville | Red Rider Stadium | Doug Davault | |||||
| 2010 | 10/30 | Wooster | 42 | 17 | W | 1 | Away | Wooster | Follis Field | Doug Davault | |||||
| 2011 | 10/29 | Wooster | 35 | 7 | W | 1 | Home | Orrville | Red Rider Stadium | Doug Davault | |||||
| 2012 | 10/27 | Wooster | 7 | 34 | L | 1 | Away | Wooster | Follis Field | Doug Davault | |||||
| 2013 | 11/2 | Wooster | 0 | 56 | L | 1 | Home | Orrville | Red Rider Stadium | Doug Davault | |||||
| 2014 | 11/1 | Wooster | 14 | 61 | L | 1 | Away | Wooster | Follis Field | Doug Davault | |||||
| 2015 | 10/30 | Wooster | 7 | 36 | L | 1 | Home | Orrville | Red Rider Stadium | Doug Davault | |||||
| 2016 | 8/25 | Wooster | 21 | 53 | L | 1 | Away | Wooster | Follis Field | Doug Davault | |||||
| 2017 | 8/25 | Wooster | 20 | 16 | W | 1 | Home | Orrville | Red Rider Stadium | Doug Davault | |||||
| 2018 | 8/24 | Wooster | 24 | 43 | L | 1 | Away | Wooster | Follis Field | Doug Davault | |||||
| 2019 | 8/30 | Wooster | 39 | 27 | W | 1 | Home | Orrville | Red Rider Stadium | Doug Davault | |||||
| 2021 | 8/20 | Wooster | 6 | 30 | L | 1 | Home | Orrville | Red Rider Stadium | Matt Zuercher | |||||
| 2022 | 8/19 | Wooster | 13 | 40 | L | 1 | Away | Wooster | Follis Field | Matt Zuercher | |||||
| 2023 | 8/18 | Wooster | 31 | 33 | L | 1 | Home | Orrville | Red Rider Stadium | Matt Zuercher | |||||
| 2024 | 8/23 | Wooster | 41 | 12 | W | 1 | Away | Wooster | Follis Field | Matt Zuercher | |||||
| 2025 | 8/22 | Wooster | 56 | 23 | W | 1 | Home | Orrville | Red Rider Stadium | Brent Besancon | |||||
| 2026 | 8/21 | Wooster | Away | Wooster | Follis Field | Brent Besancon | |||||||||
| 1,643 | 2,137 | 46 | 60 | 9 | .439 | ||||||||||
| 14.29 | 18.58 | 4.30 | |||||||||||||