In 1983 Highlands was going for it's 3rd straight class 3A State Championship. They were 10-0 and had won 35 (?) straight games or somewhere around that number.
For some reason, (rule has been changed since) they had to travel to Conner even though they were number 1 in the district. They lost 13-6 in a heartbreaking game, Bill Herman's last as the coach. Melvin Miles for Conner had 65 yard run to highlight this monumental upset. Conner went on to win what I believe is their only State Title.
Since we are on the subject, would Highlands 1992 defeat of CovCath be the Colonel's "worst" defeat? CovCath had defeated Moeller that season and handed the Bird's a loppsided loss in their first meeting.