| 2011 | Sep 1, 2011 | Massachusetts 24, Holy Cross 16 | Fitton Field · Worcester, MA |
| 2010 | Sep 11, 2010 | Massachusetts 31, Holy Cross 7 | – |
| 2008 | Sep 6, 2008 | Massachusetts 45, Holy Cross 42 | Fitton Field · Worcester, MA |
| 2007 | Sep 1, 2007 | Massachusetts 40, Holy Cross 30 | – |
| 1981 | Sep 19, 1981 | Massachusetts 13, Holy Cross 10 | – |
| 1980 | Nov 8, 1980 | Massachusetts 17, Holy Cross 13 | – |
| 1979 | Nov 10, 1979 | Holy Cross 20, Massachusetts 18 | – |
| 1978 | Nov 11, 1978 | Massachusetts 33, Holy Cross 8 | – |
| 1977 | Nov 5, 1977 | Massachusetts 28, Holy Cross 6 | – |
| 1976 | Nov 6, 1976 | Massachusetts 21, Holy Cross 14 | – |
| 1975 | Nov 8, 1975 | Massachusetts 45, Holy Cross 13 | – |
| 1974 | Nov 9, 1974 | Holy Cross 30, Massachusetts 20 | – |
| 1973 | Sep 8, 1973 | Holy Cross 30, Massachusetts 28 | – |
| 1972 | Nov 4, 1972 | Holy Cross 28, Massachusetts 16 | – |
| 1971 | Nov 6, 1971 | Massachusetts 38, Holy Cross 27 | – |
| 1970 | Nov 7, 1970 | Massachusetts 29, Holy Cross 13 | – |
| 1968 | Nov 9, 1968 | Holy Cross 47, Massachusetts 20 | – |
| 1966 | Nov 5, 1966 | Holy Cross 16, Massachusetts 14 | – |
| 1965 | Nov 6, 1965 | Massachusetts 27, Holy Cross 0 | – |
| 1964 | Nov 7, 1964 | Massachusetts 25, Holy Cross 6 | – |
| 1961 | Nov 11, 1961 | Holy Cross 44, Massachusetts 7 | – |
| 1906 | Sep 22, 1906 | Holy Cross 6, Massachusetts 4 | – |
| 1905 | Sep 30, 1905 | Holy Cross 17, Massachusetts 0 | – |
| 1904 | Sep 24, 1904 | Massachusetts 0, Holy Cross 0 | – |
| 1903 | Sep 19, 1903 | Holy Cross 6, Massachusetts 0 | – |
| 1902 | Sep 27, 1902 | Massachusetts 0, Holy Cross 0 | – |
| 1901 | Sep 28, 1901 | Massachusetts 17, Holy Cross 0 | – |
| 1900 | Sep 22, 1900 | Holy Cross 6, Massachusetts 0 | – |
| 1899 | Sep 23, 1899 | Holy Cross 11, Massachusetts 0 | – |
