| Year | Champion | Time |
| 1935 | Joe Lewandowski (Canonsburg) | 12:15 |
| 1936 | Ed Roberts (Brentwood) | 11:59 |
| 1937 | Warren Roseborough (Brentwood) | 12:46 |
| 1938 | Mario Palmer (Canonsburg) | 12:53 |
| 1939 | Mario Palmer (Canonsburg) | 11:54 |
| 1940 | Frank Siler (Freedom) | 12:45 |
| 1941 | Earl Baughman (Georges Township) | 12:21 |
| 1942 | Robert Williams (Freedom) | 12:19 |
| 1943 | Robert Leathers (Mt. Lebanon) | 12:20 |
| 1944 | Brad Richardson (Mt. Lebanon) | 12:23 |
| 1945 | Dick Plummer (Mt. Lebanon) | 12:41 |
| 1946 | Dick Plummer (Mt. Lebanon) | 12:26 |
| 1947 | Richard Ritel (Ambridge) | 12:15 |
| 1948 | Tom Sargeson (Aliquippa) | 11:06 |
| 1949 | Ted Przybyszewski (Ambridge) | 10:53 |
| 1950 | Bob Gross (Ambridge) | 11:11 |
| 1951 | Bob Cherry (Mt. Lebanon) | 11:09 |
| 1952 | Richard Sampson (New Castle) | 11:17 |
| 1953 | Marcel Denson (Aliquippa) | 10:55 |
| 1954 | Dale Fouser (Ambridge) | 11:07 |
| 1955 | Ron Rush (Shaler) | 11:46 |
| 1956 | Paul Sanders (New Castle ) | 11:09 |
| 1957 | Ron Engle (Canonsburg) | 11:42 |
| 1958 | Joe Thomas (Uniontown) | 11:45 |
| 1959 | Joe Thomas (Uniontown) | 11:40 |
| 1960 | William Brown (North Allegheny) | 11:03 |
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| 1996 | Dickie Hildebrand (North Allegheny) | 17:03 |
| 1997 | Tim Lentz (Derry) | 16:18 |
| 1998 | Greg Costello (Mt. Lebanon) | 16:09 |
| 1999 | Shawn Cavanaugh (Mt. Lebanon) | 16:12 |
| 2000 | Shawn Cavanaugh (Mt. Lebanon) | 16:10 |
| 2001 | Dan Mazzocco (Baldwin) | 16:18 |
| 2002 | Sam Bair (Shaler) | 16:10 |
| 2003 | James O'Toole (Mt. Lebanon) | 15:36 |
| 2004 | Ken King (Connellsville) | 16:05 |
| 2005 | Scott Van Kooten (Pittsburgh C.C.) | 16:10 |
| 2006 | Scott Van Kooten (Pittsburgh C.C.) | 15:53 |
| 2007 | David Adley (Baldwin) | 16:02 |
| 2008 | Matt Gregory (Canon-McMillan) | 15:50 |
| 2009 | Ryan Gil (North Allegheny) | 15:30 |
| 2010 | Zach Hebda (North Hills) | 15:29 |
| Year | Champion | Time |
| 1996 | Michael Sanford (Pine-Richland) | 16:33 |
| 1997 | Sam Shea (Brentwood) | 16:37 |
| 1998 | Scott Munroe (South Park) | 16:32 |
| 1999 | Scott Munroe (South Park) | 16:28 |
| 2000 | Jeremy Snodgrass (Greensburg C.C.) | 17:19 |
| 2001 | Dan Erny (Brentwood) | 17:21 |
| 2002 | Dan Erny (Brentwood) | 16:41 |
| 2003 | Zach Thomas (Quaker Valley) | 16:45 |
| 2004 | Jeff Weiss (McGuffey) | 15:37 |
| 2005 | Jake Walker (Ellwood City) | 15:48 |
| 2006 | Lucas Zarzeczny (Avonworth) | 16:06 |
| 2007 | Jonathan McElwain (Riverside) | 16:42 |
| 2008 | Omar Hyjek (Quaker Valley) | 16:20 |
| 2009 | Evan Miller (Laurel) | 16:33 |
| 2010 | L.J. Westwood (Quaker Valley) | 16:34 |