Operation Friendship
| Year | Win | Score | Loss | Score |
|---|
| 2020 | St. Mary's Prep | 70 | Cass Tech | 65 |
| 2019 | U of D Jesuit | 79 | Cass Tech | 59 |
| 2018 | U of D Jesuit | 68 | DEPSA | 63 |
| 2017 | U of D Jesuit | 65 | Cass Tech | 53 |
| 2016 | U of D Jesuit | 92 | East English Village | 76 |
| 2015 | Western | 58 | U of D Jesuit | 49 |
| 2014 | N/A | | N/A | |
| 2013 | Pershing | 74 | U. of D. Jesuit | 59 |
| 2012 | Detroit Catholic Central | 56 | M. L. King | 48 |
| 2011 | De La Salle | 55 | Southeastern | 49 |
| 2010 | Pershing | 77 | De La Salle | 50 |
| 2009 | Pershing | 82 | De La Salle | 75 |
| 2008 | St. Mary's Prep | 73 | Northwestern | 59 |
| 2007 | St. Mary's Prep | 81 | Redford | 79 |
| 2006 | Redford | 66 | St. Mary's Prep | 63 |
| 2005 | De Porres | 57 | Redford | 55 |
| 2004 | Renaissance | 61 | St. Mary's Prep | 32 |
| 2003 | Renaissance | 57 | De Porres | 50 |
| 2002 | Finney | 59 | De La Salle | 47 |
| 2001 | Detroit Catholic Central | 72 | Central | 70 |
| 2000 | St. Mary's Prep | 57 | Renaissance | 54 |
| 1999 | M. L. King | 63 | St. Mary's Prep | 55 |
| 1998 | Cass Tech | 73 | Bishop Borgess | 68 |
| 1997 | Denby | 69 | Detroit Catholic Central | 56 |
| 1996 | Pershing | 88 | Detroit Catholic Central | 69 |
| 1995 | Pershing | 58 | De Porres | 50 |
| 1994 | Murray-Wright | 79 | Detroit Catholic Central | 61 |
| 1993 | Aquinas | 59 | Cass Tech | 56 |
| 1992 | Cooley | 73 | U. of D. Jesuit | 59 |
| 1991 | Southwestern | 84 | De Porres | 55 |
| 1990 | Southwestern | 84 | Brother Rice | 51 |
| 1989 | Southwestern | 85 | Detroit Catholic Central | 44 |
| 1988 | Southwestern | 62 | De La Salle | 58 |
| 1987 | Southwestern | 92 | Bishop Borgess | 64 |
| 1986 | Northern | 60 | Aquinas | 54 |
| 1985 | De Porres | 58 | Southwestern | 57 |
| 1984 | Mackenzie | 70 | De Porres | 53 |
| 1983 | Southwestern | 53 | Detroit Catholic Central | 52 |
| 1982 | Southwestern | 57 | Brother Rice | 45 |
| 1981 | Southwestern | 67 | Brother Rice | 60 |
| 1980 | Central | 74 | Detroit Catholic Central | 45 |
| 1979 | Murray-Wright | 70 | Brother Rice | 60 |
| 1978 | Shrine | 50 | Northwestern | 50 |
| 1977 | Cass Tech | 54 | Divine Child | 69 |
| 1976 | Northeastern | 72 | Detroit Catholic Central | 44 |
| 1968 | Detroit Catholic Central | 57 | Murray-Wrigh | 45 |
| 1967 | Northwestern | 84 | Visitation | 59 |
| 1966 | Austin | 69 | Northwestern | 68 |
| 1965 | Northwestern | 71 | Holy Redeeme | 55 |
| 1964 | Northwestern | 49 | St. Paul | 42 |
| 1963 | St. Paul | 55 | Pershing | 46 |
| 1962 | Eastern | 56 | St. Paul | 30 |
| 1961 | Eastern | 56 | Detroit Catholic Central | 53 |
| 1960 | Eastern | 69 | Holy Redeeme | 52 |
| 1959 | Eastern | 56 | Holy Redeeme | 41 |
| 1958 | Austin | 63 | Northeastern | 40 |
| 1957 | Northwestern | 42 | All Saints | 32 |
| 1956 | St. Andrew | 61 | Southeastern | 58 |
| 1955 | Cass Tech | 59 | Shrine | 43 |
| 1954 | Northwestern | 53 | O. L. of Lourdes | 50 |
| 1953 | Southwestern | 43 | Mt. Carmel | 41 |
| 1947 | Miller | 47 | St. Joseph | 34 |
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