1999 Boys Varsity Soccer
Season:
| Tue, Aug 31 | Away vs Walnut Hills | L 1-2 | 0-1 |
| Sat, Sep 04 | Away vs Oak Hills | W 2-1 | 1-1 |
| Tue, Sep 07 | Home vs Covington Catholic | W 2-0 | 2-1 |
| Sat, Sep 11 | Away vs Colerain | L 0-3 | 2-2 |
| Tue, Sep 14 | Home vs Roger Bacon | T 0-0 | 2-2-1 |
| Sat, Sep 18 | Away vs Toledo St. Francis | T 2-2 | 2-2-2 |
| Tue, Sep 21 | Home vs Badin | W 3-0 | 3-2-2 |
| Thu, Sep 23 | Away vs La Salle | L 1-2 | 3-3-2 |
| Sat, Sep 25 | Home vs Lexington Catholic | L 0-1 | 3-4-2 |
| Tue, Sep 28 | Away vs Chaminade Julienne | L 0-2 | 3-5-2 |
| Sat, Oct 02 | Home vs Alter | T 0-0 | 3-5-3 |
| Tue, Oct 05 | Home vs McNicholas | W 4-0 | 4-5-3 |
| Thu, Oct 07 | Home vs Indian Hill | L 1-2 | 4-6-3 |
| Tue, Oct 12 | Away vs St. Henry | L 1-2 | 4-7-3 |
| Sat, Oct 16 | Away vs Moeller | L 0-3 | 4-8-3 |
| Sun, Oct 17 | Away vs Loveland | L 1-3 | 4-9-3 / Elder lost 3-1 in PKs after a scoreless regulation and two OT periods |
| Wed, Oct 20 | Home vs St. Xavier | L 0-1 | 4-10-3 / Make up from the regularly scheduled, rained out game of 10/9. |