| Year | Champion | Runner-Up | Score | Brackets |
| 1945 | ||||
| 1946 | ||||
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| 1968 | ||||
| 1969 | ||||
| 1970 | ||||
| 1971 | ||||
| 1972 | ||||
| 1973 | ||||
| 1974 | ||||
| 1975 | ||||
| 1976 | ||||
| 1977 | ||||
| 1978 | ||||
| 1979 | ||||
| 1980 | ||||
| 1981 | ||||
| 1982 | ||||
| 1983 | ||||
| 1984 | ||||
| 1985 | ||||
| 1986 | ||||
| 1987 | ||||
| 1988 | ||||
| 1989 | ||||
| 1990 | ||||
| 1991 | ||||
| 1992 | ||||
| 1993 | ||||
| 1994 | ||||
| 1995 | ||||
| 1996 | ||||
| 1997 | ||||
| 1998 | Brandon Tung (Shady Side Academy) | Bo Wiegand (Shady Side Academy) | 7-6 (4), 6-3 | |
| 1999 | Brandon Tung (Shady Side Academy) | Bo Wiegand (Shady Side Academy) | 0-6, 6-4, 7-6 (6) | |
| 2000 | Jim Crowell (Upper St. Clair) | Chris McCoy (Central Catholic) | 6-3, 6-1 | |
| 2001 | Jake Jopling (North Allegheny) | Brett Warren (Pine-Richland) | 6-1, 6-3 | Brackets |
| 2002 | Greg Warren (Pine-Richland) | Scott Kahler (Thomas Jefferson) | 6-4, 6-7 (5), 7-6 (2) | Brackets |
| 2003 | Scott Kahler (Thomas Jefferson) | Lee Michael Marnik (Peters Township) | 7-5, 7-6 (7-3) | Brackets |
| 2004 | Jon Spero (Shady Side Academy) | Mike Cobetto (North Allegheny) | 6-4, 6-3 | Brackets |
| 2005 | Casey Watt (Pine-Richland) | Zach Skorupka (North Allegheny) | 7-6 (2), 7-6 (6) | Brackets |
| 2006 | Zach Skorupka (North Allegheny) | Jon Spero (Shady Side Academy) | 7-6 (4), 6-1 | Brackets |
| 2007 | Casey Watt (Pine-Richland) | Rob Emig (Ambridge) | 6-1, 6-1 | Brackets |
| 2008 | Casey Watt (Pine-Richland) | Jay Jones (Upper St. Clair) | 6-2, 6-1 | Brackets |
| 2009 | Jay Jones (Upper St. Clair) | Matt Slamecka (Butler) | 6-3, 6-4 | Brackets |
| 2010 | Chris Mengel (Shady Side Academy) | Ethan Kallick (Upper St. Clair) | 6-3, 6-0 | Brackets |
| 2011 | Will Nesbitt (Butler) | Bas Van Lent (Pine-Richland) | 6-2, 4-6, 6-1 | Brackets |
| 2012 | Will Nesbitt (Butler) | Vivek Nimgaonkar (Shady Side Academy) | 6-3, 6-4 | Brackets |
| Year | Champion | Runner-Up | Score | Brackets |
| 1945 | ||||
| 1946 | ||||
| 1947 | ||||
| 1948 | ||||
| 1949 | ||||
| 1950 | ||||
| 1951 | ||||
| 1952 | ||||
| 1953 | ||||
| 1954 | ||||
| 1955 | ||||
| 1956 | ||||
| 1957 | ||||
| 1958 | ||||
| 1959 | ||||
| 1960 | ||||
| 1961 | ||||
| 1962 | ||||
| 1963 | ||||
| 1964 | ||||
| 1965 | ||||
| 1966 | ||||
| 1967 | ||||
| 1968 | ||||
| 1969 | ||||
| 1970 | ||||
| 1971 | ||||
| 1972 | ||||
| 1973 | ||||
| 1974 | ||||
| 1975 | ||||
| 1976 | ||||
| 1977 | ||||
| 1978 | ||||
| 1979 | ||||
| 1980 | ||||
| 1981 | ||||
| 1982 | ||||
| 1983 | ||||
| 1984 | ||||
| 1985 | ||||
| 1986 | ||||
| 1987 | ||||
| 1988 | ||||
| 1989 | ||||
| 1990 | ||||
| 1991 | ||||
| 1992 | ||||
| 1993 | ||||
| 1994 | ||||
| 1995 | ||||
| 1996 | ||||
| 1997 | ||||
| 1998 | ||||
| 1999 | Brett Warren (Pine-Richland) | Primo Bautista (Greensburg C.C.) | 6-0, 6-0 | |
| 2000 | Brett Warren (Pine-Richland) | John Houghton (Quaker Valley) | 6-3, 6-3 | |
| 2001 | John Houghton (Quaker Valley) | Jim Stillwagon (Sewickley Academy) | 6-0, 6-2 | Brackets |
| 2002 | John Houghton (Quaker Valley) | Dan Gal (South Park) | 6-2, 6-2 | Brackets |
| 2003 | John Houghton (Quaker Valley) | Dan Gal (South Park) | 6-4, 6-4 | Brackets |
| 2004 | Zach Skorupka (Sewickley Academy) | Dan Gal (South Park) | 7-5, 1-6, 6-2 | Brackets |
| 2005 | Alex Sinu (Quaker Valley) | Evan Stiegel (Sewickley Academy) | 6-2, 6-3 | Brackets |
| 2006 | Annie Houghton (Quaker Valley) | Peter Kaczmarek (Bishop Canevin) | 6-1, 6-0 | Brackets |
| 2007 | Alex Sinu (Quaker Valley) | Brandon Anandan (Knoch) | 6-2, 6-7 (4), 7-5 | Brackets |
| 2008 | Matt Hoch (Sewickley Academy) | Daniel Goldblum (Winchester Thurston) | 6-0, 6-3 | Brackets |
| 2009 | Daniel Goldblum (Winchester Thurston) | Eric Bradley (Mt. Pleasant) | 6-1, 4-6, 7-5 | Brackets |
| 2010 | Sarah Shashura (California) | Nathan Walch (Southmoreland) | 3-6, 6-3, 6-2 | Brackets |
| 2011 | Daniel Goldblum (Winchester Thurston) | David Cenkner (Mt. Pleasant) | 6-2, 6-4 | Brackets |
| 2012 | Colin Kaye (Sewickley Academy) | Grayson Geller (Sewickley Academy) | 6-4, 6-4 | Brackets |