View all the sectional titles won by the Highland Park Owls. Since 1919, Highland Park has won 12 sectional championships. Winning all 12 sectional titles since 1940, the Owls last won a sectional final in 2002. Highland Park won six sectional crowns from 1989 to 2002.
Highland Park Owls–Sectional Titles
| Year | Classification | Section |
| 1940 | Group II | Central |
| 1943 | Group II | Central |
| 1947 | Group II | Central |
| 1948 | Group II | Central |
| 1969 | Group I | Central |
| 1970 | Group I | Central |
| 1989 | Group I | Central |
| 1997 | Group I | Central |
| 1998 | Group I | Central |
| 1999 | Group I | Central |
| 2001 | Group I | Central |
| 2002 | Group I | Central |