Record: 5-4
Coach: Cliff Gillies
Points For: 141
Points Per Game: 15.6
Points Against: 137
Opponent Points Per Game: 15.2
The 1958 Bearcats season was a tale of two teams as streaks defined the year. Despite winning their opening game at Anacortes, the ‘Cats fell apart for the next four games. The offense couldn’t put up points and the defense proved to be largely ineffective. After dropping a close game at Lake Stevens, Monroe stood at 1-4 and looked destined to have their first losing season in almost a decade. Inexplicably, the Bearcats turned into a completely different team after the loss to the Vikings and snapped off a four game winning steak to close out the year. The offense and defense both came alive as the Bearcats ended with a 5-4 mark on the season. The ‘Cats avoided their first losing season of the decade but lost Coach Gillies in the offseason after a successful career at Monroe. Jerry Ramey would replace him as head coach the following season.
| Games | School | Opponent | Points For | Points Against | Win(s) | Loss(es) | Streak | Notes | ||
| 1 | Monroe | at | Issaquah | W | 12 | 7 | 1 | 0 | W 1 | |
| 2 | Monroe | vs | Mount Si | L | 7 | 13 | 1 | 1 | L 1 | |
| 3 | Monroe | at | Arlington | L | 6 | 39 | 1 | 2 | L 2 | |
| 4 | Monroe | vs | Twin City | L | 0 | 19 | 1 | 3 | L 3 | |
| 5 | Monroe | at | Lake Stevens | L | 19 | 20 | 1 | 4 | L 4 | |
| 6 | Monroe | vs | Concrete | W | 26 | 13 | 2 | 4 | W 1 | |
| 7 | Monroe | at | Oak Harbor | W | 20 | 7 | 3 | 4 | W 2 | |
| 8 | Monroe | vs | Langley | W | 19 | 6 | 4 | 4 | W 3 | |
| 9 | Monroe | at | Sultan | W | 32 | 13 | 5 | 4 | W 4 |
The Orange and the Black 