1999 Boys Freshman Football
Season:
| Wed, Sep 01 | Home vs Fairfield | L 6-14 | 0-1 |
| Wed, Sep 08 | Home vs Western Hills | W 18-6 | 1-1 |
| Wed, Sep 15 | Home vs Hughes | W 22-12 | 2-1 |
| Wed, Sep 29 | Home vs La Salle | W 20-6 | 3-1 |
| Wed, Oct 06 | Away vs Moeller | L 14-22 | 3-2 |
| Thu, Oct 07 | Home vs Moeller B | L 14-20 | 3-3 |
| Wed, Oct 13 | Home vs St. Xavier | W 20-14 | 4-3 |
| Thu, Oct 14 | Away vs St. Xavier B | W 20-14 | 5-3 |
| Wed, Oct 20 | Home vs Roger Bacon B | L 8-20 | 5-4 |
| Wed, Oct 27 | Away vs Oak Hills | W 40-6 | 6-4 |