PIAA Boys’ Swimming & Diving Individual Champions – 50 Freestyle
| Year | Winner (School) | Class | Championship Time & Runner-Up |
| 2023 | Henry Miller (Southmoreland) | 2A | 20.16; def. Noah Powers (Blue Mountain) by 0.26 |
| 2021 | Ian Shahan (Belle Vernon) | 2A | 20.00*; def. Conner McBeth (Neshannock) by 0.26 |
| 2018 | Mason Gonzalez (North Allegheny) | 3A | 19.99 |
| 2017 | Mason Gonzalez (North Allegheny) | 3A | 19.99 |
| 2015 | Francis Folz (Mars) | 2A | 21.41 |
| 2009 | Chuck Destro (Central Catholic) | 3A | 20.36 |
| Mark Stepanian (Blackhawk) | 2A | 20.86 | |
| 2004 | Brett Murphy (Shady Side Acad.) | 2A | 21.23 |
| 1997 | Michael Demos (Elizabeth Forward) | 3A | 20.82 |
| 1996 | Jerry Koller (Bethel Park) | 3A | 20.61 |
| 1989 | Brian Wolf (Bethel Park) | 21.26 | |
| 1982 | Bruce Rea (Bethel Park) | 21.43 | |
| 1980 | Mark O’Mahony (Moon) | 21.41 | |
| 1978 | Rick Carter (Shaler) | 21.61 | |
| 1977 | Mike Kriley (Butler) | 21.62 | |
| 1974 | Mark Hefren (Upper St. Clair) | 21.78 |
* – Denotes PIAA record.
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