The 1998–99 Wright State Raiders men's basketball team represented Wright State University in the 1998–99 NCAA Division I men's basketball season led by head coach Ed Schilling.

Seniors Keion Brooks and Sherman Curry returned two of the top three scorers from the previous season to anchor the squad and newcomers Kevin Melson, Marcus May and Israel Sheinfeld provided some excitement to thrill the home fans.

[1] However, by the time the season ended with what had begun to feel like the annual elimination loss to Butler,[2] playing away from the friendly Nutter Center had become synonymous with losing.

The honeymoon was over for Coach Schilling, as supporters and media had begun to voice skepticism.

[3] After the season, he again took an aggressive stance towards his own roster promising “merciless” conditioning saying “... if they don’t want to do it, I don’t want them,”[4] which further fanned speculation as to what the internal culture must be like between coach and team.