Following shortcomings in MLS Cup '98, United took winning the league championship as their top priority entering 1999.

The success of the league double culminating two previous MLS Cups, a Supporters Shield and the CONCACAF Champions' Cup was considered the apex of being tie-free until the mid to late 2000s.

Their dominance in the league was cut short the year following strict salary cap restrictions enforced by MLS to ensure parity amongst clubs.

Consequently, it resulted in certain core United players becoming too expensive for the club to retain, weakening the squad.

With the subsequent changes to the 1999 season, United would not qualify for the MLS Cup Playoffs again until 2003.