| Year | Host | Champion | Runner-Up | Details |
|---|---|---|---|---|
| 2024 | Hill Farm | High Point (236) | Shorewood Hills (145) | Full Results |
| 2023 | Shorewood Hills | High Point (221) | Monona (170) | Full Results |
| 2022 | Goodman | High Point (236) | Ridgewood (172) | Full Results |
| 2021 | Ridgewood, Parkcrest | High Point (210) | Monona (159) | Full Results |
| 2019 | Ridgewood | High Point (208) | Ridgewood (192) | Full Results |
| 2018 | West Side | Ridgewood (238) | High Point (176) | Full Results |
| 2017 | Monona | Ridgewood (201.5) | Monona (153.5) | |
| 2016 | Maple Bluff | Ridgewood (214) | High Point (160.5) | |
| 2015 | Seminole | Parkcrest (232) | Ridgewood (210) | |
| 2014 | High Point | Ridgewood (186) | Parkcrest (185) | |
| 2013 | Nakoma | Ridgewood (214) | Parkcrest (188) | |
| 2012 | Middleton | Ridgewood (219) | Parkcrest (188.5) | |
| 2011 | Shorewood Hills | Parkcrest (226) | Seminole (176.5) | |
| 2010 | Parkcrest | Parkcrest (189.5) | Hill Farm (179) | |
| 2009 | Hill Farm | Hill Farm (212) | Middleton (181) | |
| 2008 | Hawks Landing | Hill Farm (206) | Middleton (165) | |
| 2007 | West Side | Hill Farm (174) | Ridgewood (162) | |
| 2006 | Ridgewood | Parkcrest (180) | Middleton (179) | |
| 2005 | Monona | Middleton (179) | High Point (155) | |
| 2004 | Maple Bluff | Hill Farm (202) | Seminole (174.5) | |
| 2003 | Seminole | Middleton (213.5) | Hill Farm (198) | |
| 2002 | High Point | Ridgewood (261) | Middleton (191) | |
| 2001 | Nakoma | Ridgewood (280) | Middleton (197) | |
| 2000 | Middleton | Middleton (273) | Ridgewood (251) | |
| 1999 | Shorewood Hills | Ridgewood (254.5) | Middleton (236) | |
| 1998 | Parkcrest | Middleton (353) | Ridgewood (229) | |
| 1997 | Hill Farm | Middleton (276) | Parkcrest (145) | |
| 1996 | Ridgewood | Parkcrest (224) | Middleton (213) | |
| 1995 | West Side | Parkcrest (145) | West Side (125) | |
| 1994 | Monona | Parkcrest (172) | West Side (124) | |
| 1993 | Maple Bluff | Parkcrest (145) | West Side (115) | |
| 1992 | Nakoma | Parkcrest (178) | Hill Farm (120) | |
| 1991 | Middleton | Hill Farm (129) | Parkcrest (124.5) | |
| 1990 | Shorewood | Parkcrest (131) | Monona (129) | |
| 1989 | Parkcrest | Parkcrest (155.5) | Hill Farm (140) | |
| 1988 | Hill Farm | Hill Farm (162) | Parkcrest (158) | |
| 1987 | Ridgewood | Hill Farm (162) | Parkcrest (158) | |
| 1986 | West Side | Hill Farm (182.5) | Ridgewood (149.5) | |
| 1985 | Monona | Parkcrest (178.5) | Ridgewood (158) | |
| 1984 | Nakoma | Parkcrest (146) | Ridgewood (145) | |
| 1983 | Shorewood | Hill Farm (169) | Ridgewood (154) | |
| 1982 | Parkcrest | Ridgewood (185.5) | Hill Farm (139.5) | |
| 1981 | Hill Farm | Ridgewood (153) | Hill Farm (137) | |
| 1980 | Ridgewood | Hill Farm (140) | Monona (125) | |
| 1979 | West Side | Hill Farm (156) | Parkcrest (124) | |
| 1978 | Monona | Hill Farm (200) | Parkcrest (140) | |
| 1977 | Nakoma | Hill Farm (210) | Parkcrest (147) | |
| 1976 | Parkcrest | Parkcrest (186) | Shorewood (151) | |
| 1975 | Hill Farm | Shorewood (214) | Hill Farm (155) | |
| 1974 | Ridgewood | Shorewood (172) | Ridgewood (146) | |
| 1973 | West Side | Shorewood (167) | Ridgewood (145) | |
| 1972 | Monona | Shorewood (?) | () | |
| 1971 | Shorewood | Ridgewood/Shorewood (34) | Hill Farm (26) | |
| 1970 | Parkcrest | Ridgewood (58) | West Side (?) |
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