| Year: | 1998–99 |
| Team: | Valparaiso Crusaders |
| Sport: | Basketball |
| Conference: | Mid-Continent Conference |
| Short Conf: | Mid-Con |
| Record: | 23–9 |
| Conf Record: | 10–4 |
| Hc Year: | 11th |
| Champion: | Mid-Con tournament champions |
The 1998–99 Valparaiso Crusaders men's basketball team represented Valparaiso University during the 1998–99 NCAA Division I men's basketball season. The Crusaders, led by 11th-year head coach Homer Drew, played their home games at the Athletics–Recreation Center as members of the Mid-Continent Conference. Valpo finished second in the Mid-Con regular season standings, but went on to win the Mid-Con tournament to receive an automatic bid to the NCAA tournament. As No. 15 seed in the Midwest region, the Crusaders lost to No. 2 seed Maryland, 82–60,[1] to finish with a record of 23–9 (10–4 Mid-Con).
|-!colspan=9 style=| Regular season
|-!colspan=12 style=| Mid-Con tournament|-!colspan=12 style=| NCAA tournamentSource[2]