The 1999 USL Premier Development League season was the 5th PDL season. The season began in April 1999 and ended in August 1999.
Chicago Sockers finished the season as national champions, beating Spokane Shadow 3-1 in the PDL Championship game. Jackson Chargers had finished with the best regular season record in the league, winning 14 out of their 16 games, suffering just two losses, and finishing with a +55 goal difference.
18 teams were added for the season, including 7 expansion teams and four who had returned from hiatus.
5 teams folded after the 1998 Season:
Alabama Saints and South Florida Future went on hiatus for this season.
Okanagan Valley Challenge and Victoria Umbro Select returned to the PCSL, ending their associate membership. Abbotsford Athletes In Action and Seattle Hibernian retained their membership.
Blue denotes team has won their division.
Green denotes team has won playoff spot.
Orange denotes team gets bye into semifinals as host.
* denotes team is a provisional team and does not play a full schedule.
** Wichita Blue folded during the season.
Spokane hosted the Finals and received a bye to the National Semi-Finals.