WPIAL Boys’ Swimming & Diving Champions – 50-Yard Freestyle
| Year | 3A | 2A |
| 2023 | Dominic Falcon (Hempfield Area) | Henry Miller (Southmoreland) |
| 2022 | Ben Borvendeg (Butler) | Joseph Roth (Riverside) |
| 2021 | Ben Borvendeg (Butler) | Conner McBeth (Neshannock) * Ian Shahan (Belle Vernon) * |
| 2020 | Ethan Tulenko (Norwin) | Conner McBeth (Neshannock) |
| 2019 | Gavin Mayo (Hempfield Area) | Conner McBeth (Neshannock) |
| 2018 | Mason Gonzalez (North Allegheny) | Conner McBeth (Neshannock) |
| 2017 | Mason Gonzalez (North Allegheny) | Harry Harkins (Quaker Valley) |
| 2016 | Jack Rice (Mt. Lebanon) | Matt Ramsey (Hampton) |
| 2015 | Norman Gregory (Penn Hills) | Francis Folz (Mars) |
| 2014 | Judson Shiffler (Hempfield Area) | John Paul Zimcosky (Geibel Catholic) |
| 2013 | Erik Brinkhoff (Bethel Park) | Cameron Clerici (Beaver) |
| 2012 | Erik Brinkhoff (Bethel Park) | Cameron Clerici (Beaver) |
| 2011 | Erik Brinkhoff (Bethel Park) | Jon Suarez (Beaver) |
| 2010 | Garrett Hehn (Franklin Regional) | Frank Brown (Shady Side Academy) |
| 2009 | Ryan Smrekar (Norwin) | Mark Stepanian (Blackhawk) |
| 2008 | Ryan Smrekar (Norwin) | Mark Stepanian (Blackhawk) |
| 2007 | John Nolan (North Allegheny) | David Paccapaniccia (Indiana) |
| 2006 | Alex Kubicek (Gateway) | Garet Weston (Indiana) |
| 2005 | Curtis Kelly (North Hills) | A.J. Claypool (Kittanning) |
| 2004 | Curtis Kelly (North Hills) | Brett Murphy (Shady Side Academy) |
| 2003 | Jeff Koller (Bethel Park) | James Rankin (Blackhawk) |
| 2002 | Evan Powell (North Allegheny) | Tom Bayuk (Blackhawk) |
| 2001 | Matt Drozd (North Hills) | Tom Bayuk (Blackhawk) |
| 2000 | Matt Drozd (North Hills) | Jake Thieman (Chartiers Valley) |
| 1999 | Matt Drozd (North Hills) | Tim Leonardi (McGuffey) |
| 1998 | Brett Walker (Norwin) | Tim Leonardi (McGuffey) |
| 1997 | Mike Demos (Elizabeth Forward) | Tim Leonardi (McGuffey) |
| 1996 | Jerry Koller (Bethel Park) | Mike Demos (Elizabeth Forward) |
| 1995 | Jerry Koller (Bethel Park) | Scott Campbell (Moon) |
| 1994 | Jerry Koller (Bethel Park) | Kevin Langer (Quaker Valley) |
| 1993 | Rich House (Penn Hills) | Daniel Rodgers (Charleroi) |
| 1992 | Steve Salvi (Elizabeth Forward) | |
| 1991 | Jason Kunkle (Gateway) | |
| 1990 | Steve Salvi (Elizabeth Forward) | |
| 1989 | Brian Wolf (Bethel Park) | |
| 1988 | Jon Hermansderfer (Steel Valley) | |
| 1987 | Jack Moss (Central Catholic) | |
| 1986 | Jack Moss (Central Catholic) | |
| 1985 | Chris Heinman (Butler) | |
| 1984 | Jody Pfister (Bethel Park) | |
| 1983 | Mike Ross (Mt. Lebanon) | |
| 1982 | Bruce Rea (Bethel Park) | |
| 1981 | Tim Wojtaszek (Churchill) | |
| 1980 | Cliff Hardin (Peters Township) |
Notes:
* – Denotes WPIAL co-champions.
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