The game allows the player to play a single game between any two teams in an exhibition mode, or to play a season mode as the manager of a college basketball team.[1] College Hoops '99 only supports up to two player multiplayer, unlike comparable games of the time which supported four player multiplayer.[3] The season mode contains most of the major college tournaments including early-season tournaments, although the National Invitation Tournament was not included.[3]
The game uses Fox Sports's TV set-up in order to give the player a more realistic feel to gameplay.[1] However, there is no commentary and there are no fight songs or other university-specific songs in the game.