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| Date | Opp | Result |
|---|---|---|
| 1999-12-03 | vs Fort Knox | Win 76–52 |
| 1999-12-07 | @ LaRue County | Win 62–51 |
| 1999-12-10 | @ North Bullitt | Win 49–46 |
| 1999-12-11 | @ South Central | Loss 55–64 |
| 1999-12-14 | @ Elizabethtown | Loss 72–77 |
| 1999-12-20 |
Daviess County (N)
Ohio County Invitational
|
Loss 72–84 |
| 1999-12-21 |
Valley (N)
Ohio County Invitational Tournament
|
Win 78–72 |
| 1999-12-22 |
Franklin-Simpson (N)
Ohio County Invitational Tournament
|
Win 68–46 |
| 1999-12-28 | vs Spencer County | Win 99–59 |
| 2000-01-04 | vs Hart County | Win 69–65 |
| 2000-01-07 | @ Central Hardin | Win 50–42 |
| 2000-01-11 | @ North Hardin | Win 71–50 |
| 2000-01-15 | @ Bullitt East | Loss 60–65 |
| 2000-01-21 | vs Elizabethtown | Loss 59–78 |
| 2000-01-25 | @ Bardstown | Win 84–63 |
| 2000-01-28 | @ Breckinridge County | Loss 45–57 |
| 2000-02-01 | vs Central Hardin | Win 75–73 |
| 2000-02-04 | @ Fort Knox | Win 65–52 |
| 2000-02-08 | vs North Hardin | Win 85–73 |
| 2000-02-11 | @ Nelson County | Win 81–63 |
| 2000-02-15 | @ Oldham County | Loss 61–63 |
| 2000-02-18 | vs Owensboro Catholic | Loss 38–56 |
| 2000-02-19 | vs Breckinridge County | Win 78–62 |
| 2000-02-22 | vs LaRue County | Win 75–70 |
| 2000-02-25 | vs Southern | Win 77–58 |
| 2000-03-01 |
North Hardin (N)
17th District Tournament
|
Win 74–69 |
| 2000-03-03 |
Elizabethtown (N)
17th District Tournament Championship
|
Loss 73–79 |
| 2000-03-06 |
Hart County (N)
5th Region Tournament 2OT
|
Loss 65–67 |