Scores of the football game between the Rough Riders of Theodore Roosevelt High School (also known as "Kent Roosevelt") in Kent, Ohio and the Bulldogs of Stow-Munroe Falls High School (known as Stow High School until 1991) in Stow, Ohio.
Stow victories are shaded ██ gold. Kent Roosevelt victories shaded ██ red. Ties shaded ██ silver.
| Date | Site | Winning team | Losing team | Series | Notes | ||
|---|---|---|---|---|---|---|---|
| 1953 | Stow | 20 | Kent Roosevelt | 19 | Stow 1–0 | ||
| Roosevelt begins Metro League play | |||||||
| 1954 | Kent | Stow | 20 | Kent Roosevelt | 14 | Stow 2–0 | |
| 1955 | Stow | Stow | 14 | Kent Roosevelt | 12 | Stow 3–0 | |
| 1956 | Kent | Kent Roosevelt | 31 | Stow | 7 | Stow 3–1 | |
| 1957 | Stow | Kent Roosevelt | 31 | Stow | 13 | Stow 3–2 | |
| 1958 | Kent | Kent Roosevelt | 18 | Stow | 14 | Tied 3–3 | |
| 1959 | Stow | Kent Roosevelt | 38 | Stow | 0 | Kent 4–3 | |
| 1960 | Kent | Kent Roosevelt | 38 | Stow | 0 | Kent 5–3 | |
| 1961 | Stow | Stow | 22 | Kent Roosevelt | 14 | Kent 5–4 | |
| 1962 | Kent | Stow | 18 | Kent Roosevelt | 0 | Tied 5–5 | |
| 1963 | Kent | Kent Roosevelt | 28 | Stow | 6 | Kent 6–5 | |
| 1964 | Kent | Kent Roosevelt | 26 | Stow | 0 | Kent 7–5 | |
| 1965 | Kent | Stow | 13 | Kent Roosevelt | 12 | Kent 7–6 | |
| 1966 | Stow | Kent Roosevelt | 6 | Stow | 0 | Kent 8–6 | |
| 1967 | Kent | Kent Roosevelt | 25 | Stow | 0 | Kent 9–6 | |
| 1968 | Stow | Kent Roosevelt | 14 | Stow | 6 | Kent 10–6 | |
| 1969 | Kent | Stow | 14 | Kent Roosevelt | 8 | Kent 10–7 | |
| 1970 | Stow | Stow | 14 | Kent Roosevelt | 6 | Kent 10–8 | |
| 1971 | Kent | Stow | 7 | Kent Roosevelt | 0 | Kent 10–9 | First meeting at Roosevelt Stadium |
| 1972 | Stow | Kent Roosevelt | 19 | Stow | 7 | Kent 11–9 | |
| 1973 | Kent | Stow | 24 | Kent Roosevelt | 7 | Kent 11–10 | |
| 1974 | Stow | Stow | 6 | Kent Roosevelt | 0 | Tied 11–11 | |
| 1975 | Kent | Stow | 22 | Kent Roosevelt | 13 | Stow 12–11 | |
| 1976 | Stow | Kent Roosevelt | 28 | Stow | 7 | Tied 12–12 | |
| 1977 | Kent | Kent Roosevelt | 17 | Stow | 6 | Kent 13–12 | |
| 1978 | Stow | Tie, 14–14 | Kent 13–12–1 | ||||
| 1979 | Kent | Stow | 27 | Kent Roosevelt | 24 | Tied 13–13–1 | |
| 1980 | Stow | Stow | 21 | Kent Roosevelt | 13 | Stow 14–13–1 | |
| 1981 | Kent | Kent Roosevelt | 10 | Stow | 0 | Tied 14–14–1 | |
| 1982 | Stow | Kent Roosevelt | 17 | Stow | 7 | Kent 15–14–1 | |
| 1983 | Kent | Stow | 10 | Kent Roosevelt | 0 | Tied 15–15–1 | |
| 1984 | Stow | Stow | 13 | Kent Roosevelt | 7 | Stow 16–15–1 | |
| 1985 | Kent | Kent Roosevelt | 20 | Stow | 6 | Tied 16–16–1 | |
| 1986 | Stow | Kent Roosevelt | 14 | Stow | 0 | Kent 17–16–1 | |
| 1987 | Kent | Kent Roosevelt | 27 | Stow | 0 | Kent 18–16–1 | |
| 1988 | Stow | Stow | 14 | Kent Roosevelt | 6 | Kent 18–17–1 | First meeting at Bulldog Stadium |
| 1989 | Kent | Stow | 14 | Kent Roosevelt | 3 | Tied 18–18–1 | |
| 1990 | Stow | Kent Roosevelt | 21 | Stow | 20 | Kent 19–18–1 | |
| 1991 | Kent | Kent Roosevelt | 14 | Stow-Munroe Falls | 10 | Kent 20–18–1 | |
| 1992 | Stow | Stow-Munroe Falls | 24 | Kent Roosevelt | 21 | Kent 20–19–1 | |
| 1993 | Kent | Kent Roosevelt | 13 | Stow-Munroe Falls | 6 | Kent 21–19–1 | |
| 1994 | Stow | Stow-Munroe Falls | 21 | Kent Roosevelt | 0 | Kent 21–20–1 | |
| 1995 | Kent | Stow-Munroe Falls | 26 | Kent Roosevelt | 7 | Tied 21–21–1 | |
| Metro League merged into Western Reserve Conference South Division | |||||||
| 1996 | Stow | Kent Roosevelt | 17 | Stow-Munroe Falls | 14 | Kent 22–21–1 | |
| 1997 | Kent | Kent Roosevelt | 20 | Stow-Munroe Falls | 18 | Kent 23–21–1 | |
| 1998 | Stow | Stow-Munroe Falls | 25 | Kent Roosevelt | 14 | Kent 23–22–1 | |
| 1999 | Kent | Kent Roosevelt | 13 | Stow-Munroe Falls | 10 | Kent 24–22–1 | |
| 2000 | Stow | Stow-Munroe Falls | 41 | Kent Roosevelt | 13 | Kent 24–23–1 | |
| 2001 | Kent | Stow-Munroe Falls | 28 | Kent Roosevelt | 21 | Tied 24–24–1 | |
| 2002 | Stow | Stow-Munroe Falls | 24 | Kent Roosevelt | 14 | Stow 25–24–1 | |
| 2003 | Kent | Kent Roosevelt | 24 | Stow-Munroe Falls | 7 | Tied 25–25–1 | |
| 2004 | Stow | Kent Roosevelt | 10 | Stow-Munroe Falls | 6 | Kent 26–25–1 | |
| Roosevelt leaves WRC, joins Portage Trail Conference | |||||||
| 2005 | Kent | Kent Roosevelt | 20 | Stow-Munroe Falls | 0 | Kent 27–25–1 | |
| 2006 | Stow | Kent Roosevelt | 14 | Stow-Munroe Falls | 7 | Kent 28–25–1 | |
| Western Reserve Conference merged into the Northeast Ohio Conference | |||||||
| 2007 | Kent | Stow-Munroe Falls | 45 | Kent Roosevelt | 20 | Kent 28–26–1 | |
| 2008 | Stow | Stow-Munroe Falls | 14 | Kent Roosevelt | 0 | Kent 28–27–1 | |
| 2009 | Kent | Kent Roosevelt | 21 | Stow-Munroe Falls | 17 | Kent 29–27–1 | |
| 2010 | Stow | Kent Roosevelt | 41 | Stow-Munroe Falls | 14 | Kent 30–27–1 | |
| 2011 | Kent | Kent Roosevelt | 55 | Stow-Munroe Falls | 28 | Kent 31–27–1 | |
| 2012 | Stow | Stow-Munroe Falls | 33 | Kent Roosevelt | 0 | Kent 31–28–1 | |
| 2013 | Kent | Stow-Munroe Falls | 35 | Kent Roosevelt | 14 | Kent 31–29–1 | |
| 2014 | Stow | Stow-Munroe Falls | 42 | Kent Roosevelt | 8 | Kent 31–30–1 | |
| Both teams begin play in Suburban League in opposite divisions | |||||||
| 2015 | Kent | Stow-Munroe Falls | 49 | Kent Roosevelt | 28 | Tied 31–31–1 | |
| 2016 | Stow | Stow-Munroe Falls | 56 | Kent Roosevelt | 14 | Stow 32–31–1 | |
| 2017 | Kent | Stow-Munroe Falls | 37 | Kent Roosevelt | 14 | Stow 33–31–1 | |