| Year | Record | Coach | Extra Info |
|---|---|---|---|
| 1908 | 0-3 | C.E. Stanley | West Milton HS |
| 1909 | No team | ||
| 1910 | 3-1 | A.W McArtor | |
| 1911-14 | No team | ||
| 1915 | 0-4-1 | C.E. Stanley | |
| 1916 | 5-3 | C.E. Stanley | |
| 1917 | 0-7 | C.E. Stanley | |
| 1918-20 | No team | ||
| 1921 | 1-5 | F.L. Bait | |
| 1922 | 4-3 | Wilber Fish | |
| 1923 | 10-2 | Ralph Blauvelt | |
| 1924 | 0-6 | Ralph Blauvelt | |
| 1925 | 1-6-1 | R.V. Kessler | |
| 1926 | 2-5 | R.V. Kessler | |
| 1927-1939 | No team fielded | ||
| 1938 | West Milton - Union Twp consolidate into Milton-Union | ||
| 1940 | 1-5-1 | David Longenecker | |
| 1941 | 1-6 | John Manchester | |
| 1942 | 2-4 | Beryl Hensel | |
| 1943 | 0-7 | Denny Young | |
| 1944 | 0-8 | James Jackson | |
| 1945 | 1-6-1 | James Jackson | |
| 1946 | 4-3-1 | James Jackson | |
| 1947 | 5-3-1 | Wm Holford | |
| 1948 | 9-0 | Wm Holford | SWBL Champions |
| 1949 | 5-5 | Wm Holford | |
| 1950 | 8-1 | Wm Holford | |
| 1951 | 5-3-1 | Harvey Hole | |
| 1952 | 6-3 | Harvey Hole | SWBL Champions |
| 1953 | 1-7-1 | Bob Long | |
| 1954 | 7-1-1 | Bob Long | SWBL Champions |
| 1955 | 4-5 | Bob Long | |
| 1956 | 4-5 | Bob Long | |
| 1957 | 3-4-2 | Bob Long | |
| 1958 | 3-6 | Bob Long | |
| 1959 | 8-0-1 | Bob Long | SWBL Champions |
| 1960 | 10-0 | Bob Long | SWBL Champions |
| 1961 | 8-1-1 | Bob Long | |
| 1962 | 8-1-1 | Bob Long | SWBL Champions |
| 1963 | 5-4-1 | Wat Farrar | |
| 1964 | 3-7 | Wat Farrar | |
| 1965 | 7-3 | Wat Farrar | |
| 1966 | 9-0-1 | Wat Farrar | SWBL Champions |
| 1967 | 7-2-1 | Wat Farrar | |
| 1968 | 7-3 | Wat Farrar | |
| 1969 | 10-0 | Wat Farrar | SWBL Champions |
| 1970 | 9-1 | Wat Farrar | |
| 1971 | 8-2 | Wat Farrar | SWBL Champions |
| 1972 | 8-1-1 | Wat Farrar | SWBL Champions |
| 1973 | 5-5 | Wat Farrar | |
| 1974 | 1-9 | Wat Farrar | |
| 1975 | 8-2 | Wat Farrar | SWBL Champions |
| 1976 | 5-5 | Wat Farrar | |
| 1977 | 10-0 | Wat Farrar | SWBL Champions |
| 1978 | 10-0 | Steve Magoteaux | SWBL Champions |
| 1979 | 8-2 | Steve Magoteaux | SWBL Champions |
| 1980 | 6-4 | Steve Magoteaux | |
| 1981 | 9-1 | Steve Magoteaux | SWBL Champions |
| 1982 | 10-0 | Steve Magoteaux | SRC Champions |
| 1983 | 7-3 | Steve Magoteaux | |
| 1984 | 3-7 | Tom Adams | |
| 1985 | 4-6 | Tom Adams | |
| 1986 | 5-5 | Wat Farrar | |
| 1987 | 4-6 | Wat Farrar | |
| 1988 | 4-6 | Wat Farrar | |
| 1989 | 4-6 | Wat Farrar | |
| 1990 | 6-4 | Ken Christello | |
| 1991 | 4-6 | Ken Christello | |
| 1992 | 5-5 | Ken Christello | |
| 1993 | 4-6 | Ken Christello | |
| 1994 | 0-10 | Ken Christello | |
| 1995 | 3-7 | Tony Sergent | |
| 1996 | 3-7 | Tony Sergent | |
| 1997 | 5-5 | Gary Rip Engle | |
| 1998 | 6-4 | Gary Rip Engle | |
| 1999 | 3-7 | Rip Engle | |
| 2000 | 1-9 | Bret Pearce | |
| 2001 | 1-9 | Bret Pearce | |
| 2002 | 7-4 | Bret Pearce | Playoffs |
| 2003 | 5-5 | Bret Pearce | |
| 2004 | 3-6 | Bret Pearce | |
| 2005 | 8-3 | Bret Pearce | Playoffs |
| 2006 | 11-2 | Bret Pearce | SWBL Champions, Playoffs, Regional Runner-ups |
| 2007 | 10-2 | Bret Pearce | SWBL Champions, Playoffs |
| 2008 | 3-7 | Bret Pearce | |
| 2009 | 6-4 | Bret Pearce | |
| 2010 | 4-6 | Bret Pearce | |
| 2011 | 8-3 | Bret Pearce | Playoffs |
| 2012 | 10-3 | Bret Pearce | SWBL Champions, Playoffs, Regional Runner-ups |
| 2013 | 2-8 | Mark Lane | |
| 2014 | 3-7 | Mark Lane | |
| 2015 | 6-5 | Mark Lane | Playoffs |
| 2016 | 8-4 | Mark Lane | Playoffs |
| 2017 | 4-6 | Mark Lane | |
| 2018 | 6-4 | Bret Pearce | |
| 2019 | 8-3 | Bret Pearce | Playoffs |
| 2020 | 7-3 | Bret Pearce | Playoffs |
| 2021 | 10-2 | Bret Pearce | Playoffs; 1st year in TRC |
| 2022 | 13-1 | Bret Pearce | Playoffs, Regional Runner-ups |
| 2023 | 7-4 | Bret Pearce | Playoffs |
| 2024 | 6-5 | Bret Pearce | Playoffs |