| PENN TOURNAMENT HISTORY |
| SECTIONALS (14) |
| YEAR | WINNER | SITE OR HOST | CLASS |
| 1965 | Penn | Elkhart | |
| 1968 | Penn | Elkhart | |
| 1972 | Penn | Elkhart | |
| 1973 | Penn | Elkhart Central | |
| 1983 | Penn | Elkhart Central | |
| 1984 | Penn | Elkhart Central | |
| 1987 | Penn | Elkhart Central | |
| 1992 | Penn | Elkhart Central | |
| 1996 | Penn | Elkhart Central | |
| 1999 | Penn | Penn | 4A |
| 2000 | Penn | Penn | 4A |
| 2001 | Penn | South Bend Riley | 4A |
| 2006 | Penn | Elkhart Central | 4A |
| 2007 | Penn | Elkhart Central | 4A |
| REGIONALS (6) |
| 1972 | Penn | Elkhart | |
| 1987 | Penn | Elkhart Central | |
| 1999 | Penn | Michigan City | 4A |
| 2000 | Penn | Penn | 4A |
| 2001 | Penn | Portage | 4A |
| 2006 | Penn | Michigan City | 4A |
| SEMISTATES (1) |
| 2001 | Penn | West Lafayette | 4A |