1998-1999 Kirkwood Pioneers
| Kirkwood | 52 | Ladue | 35 |
| Kirkwood | 55 | Pattonville | 39 |
| Kirkwood | 66 | Webster Groves | 54 |
| Kirkwood | 76 | Seckman | 46 |
| Kirkwood | 72 | Rockwood Summit | 45 |
| Kirkwood | 65 | Lindbergh | 37 |
| Kirkwood | 61 | Marquette | 32 |
| Kirkwood | 55 | St. Louis University | 57 |
| Kirkwood | 55 | Vianney North | 69 |
| Kirkwood | 74 | Fox | 53 |
| Kirkwood | 76 | Hazelwood East | 58 |
| Kirkwood | 57 | Parkway South | 42 |
| Kirkwood | 61 | Hazelwood Central | 56 |
| Kirkwood | 56 | Parkway West | 58 |
| Kirkwood | 50 | Lafayette | 53 |
| Kirkwood | 74 | Mehlville | 43 |
| Kirkwood | 65 | Ritenour | 26 |
| Kirkwood | 60 | Parkway Central | 58 |
| Lafayette Tournament | |||
| Kirkwood | 44 | Lafayette | 53 |
| Kirkwood | 58 | Eureka | 54 |
| Meramec Tournament | |||
| Kirkwood | 45 | Parkway South | 49 |
| Kirkwood | 41 | Oakville | 30 |
| Kirkwood | 70 | Webster | 44 |
| Kirkwood | 49 | Parkway West | 50 |
| District Tournament | |||
| Kirkwood | 47 | Marquette | 44 |
| Kirkwood | 79 | Vianney | 61 |
| Kirkwood | 43 | Parkway South | 40 |
| Sectionals | |||
| Kirkwood | 55 | Sikeston | 45 |
| Quarterfinals | |||
| Kirkwood | 34 | DeSmet | 63 |
Head Coach: Randy Kriewall
Henok Tekle (manager)
Kevin Moulder
Darrell Redmond
Randy Holbrook
Darrell Lee
Sean Worrall
Ty Fagan
Andrew Murray
Terrence Curry
Patrick Mullen
Eric Walden
Joshua Frick
Daniel Murray
Antoine Smith
Anthony Smith