Kobe Bryant in NBA Courtside features 5-on-5 gameplay. There are three modes: Pre-Season (Exhibition), Season, and Playoffs. In both Season and Playoffs modes, players have the option to simulate games.
Team rosters reflect the 1997-98 NBA season with two notable omissions: Chicago Bulls superstar Michael Jordan, and Golden State Warriors star Latrell Sprewell. Due to licensing agreements, a fictional player named "Roster Player #98" is used in Jordan's place. Upon the game's release, Sprewell was serving a 68-game suspension from the league (see: 1997 choking incident).