NBA All-Star Challenge is the first game in the series of the same name, offering one-on-one basketball featuring licensed NBA players. The game features five different mini-games based on real-life one-on-one playing modes. All can be played by two players via the link cable.

The modes are:

One On One: two players attack the same basket, alternating on offense and defense, playing to either a time or a score limit (both adjustable).
Free Throws: one player gets either 5, 10 or 20 throws. A crosshair moves over the board automatically and the button has to be pressed at the right position to make the shot.
Horse: One player has to replicate the other player's shot from the same position or gain a letter in the word H-O-R-S-E. The first player to complete the word loses.
Accuracy Shootout: Within an adjustable time limit, shots must be made from set positions for maximum score.
Tournament: a One On One tournament in knock-out mode, featuring eight players total.

For each mode, players can select from 27 different players (one per NBA team of the 1989-1990 season), featuring the likes of Michael Jordan, Patrick Ewing, Larry Bird, and Isiah Thomas.