| HIGHLAND BULLDOG CROSS COUNTRY "FIRSTS" | ||
| 1952 | First recognized cross country season | |
| 1970 | First perfect score (15) recorded | (vs. O'Fallon) |
| 1970 | First invitational championship | Bunker Hill |
| 1971 | First IHSA State Meet appearance | Boys team |
| 1973 | First Mississippi Valley Conference (MVC) titile | Boys team |
| 1974 | First undefeated season (21-0) | Boys team |
| 1974 | First individual MVC champion | Keith Byers |
| 1975 | First girls participate in cross country | |
| 1979 | First recognized girls cross country season | |
| 1979 | First girls Mississippi Valley Conference title | Girls team |
| 1979 | First girls individual MVC champion | Julie Curry |
| 1979 | First All-state cross country individual | Julie Curry |
| 1981 | First boys All-state cross country individual | Darryl Frerker |
| 1989 | First Madison County Team Champion | Girls team |
| 1991 | First boys Madison County Team Champion | Boys team |
| 1992 | First IHSA Regional Team Champion | Girls team |
| 1992 | First Girls Team IHSA State Meet appearance | Girls team |
| 1993 | First four-year IHSA state qualifier | Janelle Torbit |
| 1999 | First Mississippi Valley Conference title sweep | Boys & Girls team |
| 2001 | First boys IHSA Regional Team Champion | Boys team |
| 2001 | First perfect score in MVC championship meet | Boys team |
| HIGHLAND BULLDOG HEAD COACHES | ||
| 1952-1957 | Olin Stratton | |
| 1958-1967 | Ed Hilbert | |
| 1968-1976 | Fred Singleton | |
| 1977-1983 | Steve Moore | |
| 1984-1985 | Ted Cipicchio | |
| 1986-1993 | Brad Hyre | |
| 1994-1996 | Mark Geppert | |
| 1997-2005 | Brad Hyre | |
2006- |
Doug Bradley | |