Starting with NHL 99 up to NHL 2001 there were very few large improvements to the game. NHL 99 for the PlayStation boasted higher-resolution graphics than NHL 98, but the framerate and unresponsive controls (especially in 2+ player modes) hindered its playability. A career mode (later developed into a Franchise mode) with a retirement feature, drafting, and player trades were added to the game. Furthermore, created players can use any photo for their face which is textured onto the head. Online leagues of the game also became more organized. Daryl Reaugh left the series as color commentator following NHL 99. Jim Hughson remained as play-by-play announcer in the game.

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