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.

15 seed in the Midwest region, the Crusaders lost to No.

2 seed Maryland, 82–60,[2] to finish with a record of 23–9 (10–4 Mid-Con).