WPIAL Boys’ Swimming & Diving Champions – 100-Yard Freestyle
| Year | 3A | 2A |
| 2023 | Patton Graziano (Penn-Trafford) | Conner McBeth (Neshannock) |
| 2022 | Daniel Simoes (Seneca Valley) | Preston Kessler (Indiana) |
| 2021 | Joshua Bogniard (North Hills) | Conner McBeth (Neshannock) |
| 2020 | Branko Kosanovich (North Allegheny) | Ian Shahan (Belle Vernon) |
| 2019 | Kimani Gregory (Penn Hills) | Ian Shahan (Belle Vernon) |
| 2018 | Kimani Gregory (Penn Hills) | Conner McBeth (Neshannock) |
| 2017 | Mason Gonzalez (North Allegheny) | Harry Harkins (Quaker Valley) |
| 2016 | Mason Gonzalez (North Allegheny) | Matt Kwalick (Quaker Valley) |
| 2015 | Brian Lovasik (North Hills) | Matt Ramsey (Hampton) |
| 2014 | Brian Lovasik (North Hills) | Francis Folz (Mars) |
| 2013 | Alex Hardwick (Upper St. Clair) | Cameron Clerici (Beaver) |
| 2012 | Lucas Bureau (Greater Latrobe) | Cameron Clerici (Beaver) |
| 2011 | Lucas Bureau (Greater Latrobe) | Broderick Kelley (Shady Side Academy) |
| 2010 | Garrett Hehn (Franklin Regional) | Frank Brown (Shady Side Academy) |
| 2009 | Sho Sugimoto (Mt. Lebanon) | Mark Stepanian (Blackhawk) |
| 2008 | Sho Sugimoto (Mt. Lebanon) | David Paccapaniccia (Indiana) |
| 2007 | Matt Scherer (North Allegheny) | Trevor Scheid (Shady Side Academy) |
| 2006 | Raymond Toomey (Baldwin) | Andrew Zaydak (Saint Joseph) |
| 2005 | Curtis Kelly (North Hills) | Tyler Scheid (Shady Side Academy) |
| 2004 | Curtis Kelly (North Hills) | Brett Murphy (Shady Side Academy) |
| 2003 | Alan Carter (Bethel Park) | Brett Murphy (Shady Side Academy) |
| 2002 | Alan Carter (Bethel Park) | Brett Murphy (Shady Side Academy) |
| 2001 | Matt Drozd (North Hills) | Brett Murphy (Shady Side Academy) |
| 2000 | Patrick Dinan (Peters Township) * David Ruch (Bethel Park) * |
Bob McGrath (Hampton) |
| 1999 | David Ruch (Bethel Park) | Tim Leonardi (McGuffey) |
| 1998 | Brett Walker (North Hills) | Tim Leonardi (McGuffey) |
| 1997 | Mike Demos (Elizabeth Forward) | Rob Gallagher (Steel Valley) |
| 1996 | Jerry Koller (Bethel Park) | Brendan Lupetin (Shady Side Academy) |
| 1995 | Jerry Koller (Bethel Park) | Brendan Lupetin (Shady Side Academy) |
| 1994 | Jerry Koller (Bethel Park) | Kevin Langer (Quaker Valley) |
| 1993 | Jason James (Bethel Park) | Kevin Langer (Quaker Valley) |
| 1992 | Jason James (Bethel Park) | |
| 1991 | Jason Kunkle (Gateway) | |
| 1990 | Craig Uzelac (Fox Chapel) | |
| 1989 | Clyde Lundgren (Bethel Park) | |
| 1988 | Clyde Lundgren (Bethel Park) | |
| 1987 | Clyde Lundgren (Bethel Park) | |
| 1986 | Kurt Lundgren (Bethel Park) | |
| 1985 | Mike Miklus (Plum) | |
| 1984 | Doug Watson (Norwin) | |
| 1983 | Steve Francis (Shaler) | |
| 1982 | Bruce Rea (Bethel Park) | |
| 1981 | Bruce Rea (Bethel Park) | |
| 1980 | Randy Potter (North Allegheny) |
Notes:
* – Denotes WPIAL co-champions.
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