1999-2000 Boys Varsity Basketball
Season:
| Fri, Dec 03 | Away vs St. Henry | W 71-47 | 1-0 |
| Fri, Dec 10 | Away vs Badin | W 56-35 | 2-0 |
| Tue, Dec 14 | Home vs Roger Bacon | W 71-48 | 3-0 |
| Fri, Dec 17 | Away vs Moeller | W 65-56 | 4-0 / Kelsey 21 points |
| Tue, Dec 21 | Home vs Holy Cross | W 85-46 | 5-0 |
| Mon, Dec 27 | Away vs Cleveland St. Ignatius | L 62-64 | 5-1 / Kelsey 23 points |
| Tue, Dec 28 | Away vs Cleveland Bedford | W 78-64 | 6-1 |
| Tue, Jan 04 | Away vs Oak Hills | W 66-60 | 7-1 / Kelsey 20 points |
| Fri, Jan 07 | Home vs La Salle | W 55-49 | 8-1 / Kelsey 30 points |
| Mon, Jan 10 | Away vs Western Hills | W 63-57 | 9-1 |
| Fri, Jan 14 | Away vs St. Xavier | L 42-46 | 9-2 |
| Tue, Jan 18 | Away vs Purcell-Marian | L 56-57 | 9-3 |
| Fri, Jan 21 | Home vs Chaminade Julienne | W 74-70 | 10-3 / Mahon 31 points |
| Tue, Jan 25 | Away vs Kettering Alter | L 54-55 | 10-4 |
| Fri, Jan 28 | Home vs McNicholas | W 63-48 | 11-4 / Kelsey 24 points |
| Fri, Feb 04 | Home vs Moeller | W 63-58 | 12-4 |
| Sat, Feb 05 | Home vs Toledo Scott | W 79-62 | 13-4 |
| Fri, Feb 11 | Away vs La Salle | W 62-40 | 14-4 / Kelsey 23 points |
| Tue, Feb 15 | Home vs Covington Catholic | W 54-48 | 15-4 |
| Fri, Feb 18 | Home vs St. Xavier | W 48-45 | 16-4 |
| Wed, Mar 01 | Home vs Northwest | W 52-35 | 17-4 / Sectional Tournament; Kelsey 27 points |
| Mon, Mar 06 | Home vs Western Hills | W 56-54 | 18-4 / Sectional Tournament; Bazeley 21 points |
| Sat, Mar 11 | Home vs Lakota West | W 67-49 | 19-4 / Sectional Tournament |
| Thu, Mar 16 | Home vs St. Xavier | L 45-55 | 19-5 / Sectional Tournament; Kelsey 21 points |