First meeting: Nov. 17, 1923 - Ridgefield 13, Woodland 0
Latest meeting: Oct. 31, 2025 - Ridgefield 17, Woodland 16
Next meeting: 2026
Meetings total: 106
All-time series: Tied 51-51-4
League series: Woodland Leads 45-38-2
Post-season series: n/a
Largest victory: Woodland, 47-0 (1949)
Longest win streak: Ridgefield, 9 (1939-1944)
Current win streak: Ridgefield, 1 (2025-present)
| Ridgefield Victories | Woodland Victories | Tie Games |
| No. | Date | Winning Team | Losing Team | |||
| 1 | Nov. 17, 1923 | at Ridgefield | 13 | Woodland | 0 | |
| 2 | Oct. 28, 1924 | at Woodland | 13 | Ridgefield | 6 | |
| 3 | Nov. 4, 1924 | at Ridgefield | Woodland | |||
| 4 | Oct. 29, 1926 | at Ridgefield | 19 | Woodland | 0 | |
| 5 | Oct. 21, 1927 | Ridgefield | 27 | at Woodland | 0 | |
| 6 | Oct. 8, 1929 | Ridgefield | 19 | at Woodland | 0 | |
| 7 | Nov. 9, 1929 | at Ridgefield | 18 | Woodland | 0 | |
| 8 | Oct. 3, 1930 | Ridgefield | 13 | at Woodland | 0 | |
9 |
Nov. 27, 1930 | Ridgefield | 13 | at Woodland | 6 | |
| 10 | Sept. 18, 1931 | Woodland | 7 | at Ridgefield | 6 | |
| 11 | Sept. 23, 1932 | at Woodland | 12 | Ridgefield | 0 | |
| 12 | Nov. 24, 1932 | Woodland | 0 | at Ridgefield | 0 | TIE |
| 13 | Sept. 15, 1933 | at Ridgefield | 6 | Woodland | 0 | |
| 14 | Sept. 19, 1934 | Woodland | 6 | at Ridgefield | 0 | |
| 15 | Oct. 12, 1934 | Woodland | 12 | at Ridgefield | 0 | |
| 16 | Oct. 11, 1935 | Woodland* | 25 | at Ridgefield | 6 | |
| 17 | Sept. 16, 1938 | Woodland | 6 | at Ridgefield | 6 | TIE |
| 18 | Nov. 23, 1939 | Ridgefield* | 14 | at Woodland | 6 | |
| 19 | Nov. 21, 1940 | at Ridgefield* | 34 | Woodland | 0 | |
| 20 | Nov. 20, 1941 | Ridgefield* | 12 | at Woodland | 0 | |
| 21 | Oct. 30, 1942 | Ridgefield* | 19 | at Woodland | 0 | |
| 22 | Nov. 26, 1942 | at Ridgefield | 12 | Woodland | 0 | |
| 23 | Oct. 22, 1943 | at Ridgefield* | 26 | Woodland | 0 | |
| 24 | Nov. 25, 1943 | Ridgefield* | 6 | at Woodland | 0 | |
| 25 | Oct. 13, 1944 | Ridgefield* | 32 | at Woodland | 0 | |
| 26 | Nov. 23, 1944 | at Ridgefield* | 40 | Woodland | 0 | |
| 27 | Nov. 16, 1945 | at Woodland* | 6 | Ridgefield | 0 | |
| 28 | Nov. 1, 1946 | at Ridgefield* | 13 | Woodland | 12 | |
| 29 | Sept. 26, 1947 | Ridgefield* | 14 | at Woodland | 13 | |
| 30 | Oct. 29, 1948 | at Ridgefield* | 34 | Woodland | 7 | |
| 31 | Oct. 21, 1949 | at Woodland* | 47 | Ridgefield | 0 | |
| 32 | Oct. 13, 1950 | at Ridgefield* | 6 | Woodland | 0 | |
| 33 | Sept. 21, 1951 | Ridgefield* | 32 | at Woodland | 12 | |
| 34 | Sept. 19, 1952 | at Ridgefield* | 19 | Woodland | 6 | |
| 35 | Sept. 18, 1953 | at Woodland* | 21 | Ridgefield | 0 | |
| 36 | Oct. 15, 1954 | Woodland* | 27 | at Ridgefield | 0 | ** |
| 37 | Sept. 16, 1955 | at Woodland* | 34 | Ridgefield | 12 | |
| 38 | Sept. 14, 1956 | Woodland* | 19 | at Ridgefield | 6 | |
| 39 | Oct. 11, 1957 | Ridgefield* | 20 | at Woodland | 6 | |
| 40 | Nov. 11, 1958 | Woodland* | 46 | at Ridgefield | 26 | |
| 41 | Nov. 13, 1959 | at Woodland* | 34 | Ridgefield | 0 | |
| 42 | Nov. 4, 1960 | Woodland* | 26 | at Ridgefield | 0 | |
| 43 | Nov. 3, 1961 | Ridgefield* | 7 | at Woodland | 7 | TIE |
| 44 | Nov. 2, 1962 | Woodland* | 0 | at Ridgefield | 0 | TIE |
| 45 | Sept. 27, 1963 | Ridgefield* | 41 | at Woodland | 0 | |
| 46 | Sept. 25, 1964 | at Ridgefield* | 20 | Woodland | 6 | |
| 47 | Sept. 24, 1965 | Ridgefield* | 26 | at Woodland | 7 | |
| 48 | Sept. 23, 1966 | Woodland* | 12 | at Ridgefield | 6 | |
| 49 | Sept. 22, 1967 | at Woodland* | 26 | Ridgefield | 6 | |
| 50 | Nov. 1, 1968 | at Woodland* | 19 | Ridgefield | 0 | |
| 51 | Oct. 31, 1969 | at Ridgefield* | 21 | Woodland | 6 | |
| 52 | Oct. 30, 1970 | at Woodland* | 37 | Ridgefield | 6 | |
| 53 | Oct. 22, 1971 | at Ridgefield | 27 | Woodland | 0 | |
| 54 | Oct. 13, 1972 | at Woodland* | 33 | Ridgefield | 6 | |
| 55 | Sept. 28, 1973 | Woodland | 21 | at Ridgefield | 6 | |
| 56 | Nov. 2, 1973 | at Woodland* | 24 | Ridgefield | 18 | |
| 57 | Oct. 25, 1974 | at Woodland* | 28 | Ridgefield | 6 | |
| 58 | Oct. 17, 1975 | Woodland* | 6 | at Ridgefield | 0 | |
| 59 | Oct. 15, 1976 | Ridgefield* | 6 | at Woodland | 0 | |
| 60 | Oct. 7, 1977 | at Ridgefield* | 8 | Woodland | 6 | 2 OT |
| 61 | Sept. 29, 1978 | Ridgefield* | 13 | at Woodland | 7 | |
| 62 | Sept. 21, 1979 | Woodland* | 21 | at Ridgefield | 12 | |
| 63 | Nov. 7, 1980 | at Woodland* | 21 | Ridgefield | 6 | |
| 64 | Oct. 30, 1981 | at Woodland* | 26 | Ridgefield | 6 | |
| 65 | Oct. 29, 1982 | at Ridgefield* | 9 | Woodland | 6 | |
| 66 | Oct. 14, 1983 | at Woodland* | 26 | Ridgefield | 13 | |
| 67 | Oct. 19, 1984 | Woodland* | 14 | at Ridgefield | 6 | |
| 68 | Oct. 25, 1985 | at Woodland* | 13 | Ridgefield | 7 | |
| 69 | Oct. 24, 1986 | Woodland* | 14 | at Ridgefield | 13 | |
| 70 | Oct. 30, 1987 | at Woodland* | 13 | Ridgefield | 7 | |
| 71 | Oct. 28, 1988 | Woodland* | 14 | at Ridgefield | 7 | |
| 72 | Sept. 29, 1989 | at Ridgefield* | 12 | Woodland | 7 | |
| 73 | Sept. 28, 1990 | Ridgefield* | 19 | at Woodland | 7 | |
| 74 | Nov. 1, 1991 | Ridgefield* | 41 | at Woodland | 0 | |
| 75 | Oct. 30, 1992 | at Ridgefield* | 46 | Woodland | 7 | |
| 76 | Nov. 5, 1993 | at Woodland* | 25 | Ridgefield | 15 | |
| 77 | Nov. 3, 1994 | at Ridgefield* | 49 | Woodland | 6 | |
| 78 | Sept. 22, 1995 | at Ridgefield* | 35 | Woodland | 14 | |
| 79 | Sept. 27, 1996 | Ridgefield* | 30 | at Woodland | 15 | |
| 80 | Oct. 24, 1997 | at Woodland* | 40 | Ridgefield | 24 | |
| 81 | Oct. 24, 1998 | Woodland* | 16 | at Ridgefield | 13 | |
| 82 | Nov. 5, 1999 | at Woodland* | 27 | Ridgefield | 18 | |
| 83 | Nov. 3, 2000 | Woodland* | 31 | at Ridgefield | 24 | |
| 84 | Sept. 28, 2001 | Woodland* | 13 | at Ridgefield | 7 | |
| 85 | Sept. 20, 2002 | Ridgefield* | 25 | at Woodland | 14 | |
| 86 | Sept. 19, 2003 | at Ridgefield* | 30 | Woodland | 7 | |
| 87 | Sept. 17, 2004 | at Woodland* | 9 | Ridgefield | 7 | |
| 88 | Sept. 16, 2005 | at Ridgefield* | 27 | Woodland | 21 | |
| 89 | Oct. 27, 2006 | at Woodland* | 28 | Ridgefield | 14 | |
| 90 | Oct. 26, 2007 | Woodland* | 42 | at Ridgefield | 6 | |
| 91 | Oct. 31, 2008 | at Woodland* | 33 | Ridgefield | 0 | |
| 92 | Oct. 30, 2009 | Woodland* | 41 | at Ridgefield | 14 | |
| 93 | Sept. 10, 2010 | Ridgefield | 27 | at Woodland | 7 | |
| 94 | Sept. 9, 2011 | at Ridgefield | 27 | Woodland | 20 | |
| 95 | Sept. 26, 2014 | Woodland* | 48 | at Ridgefield | 15 | |
| 96 | Sept. 25, 2015 | Ridgefield* | 60 | at Woodland | 27 | |
| 97 | Oct. 21, 2016 | at Woodland* | 38 | Ridgefield | 16 | |
| 98 | Oct. 20, 2017 | Woodland* | 40 | at Ridgefield | 16 | |
| 99 | Oct. 12, 2018 | at Woodland* | 42 | Ridgefield | 21 | |
| 100 | Oct. 18, 2019 | at Ridgefield* | 34 | Woodland | 6 | |
| 101 | Mar. 19, 2021 | at Woodland* | 26 | Ridgefield | 7 | |
| 102 | Oct. 29, 2021 | at Ridgefield* | 47 | Woodland | 14 | |
| 103 | Oct. 28, 2022 | Ridgefield* | 31 | at Woodland | 14 | |
| 104 | Oct. 27, 2023 | Woodland* | 28 | at Ridgefield | 21 | |
| 105 | Nov. 1, 2024 | at Woodland* | 14 | Ridgefield | 7 | |
| 106 | Oct. 31, 2025 | at Ridgefield* | 17 | Woodland | 16 | |
** 1954 game ended in the 3rd qtr due to a county-wide power outage.

