It took place on November 21, 1999, at Foxboro Stadium in Foxborough, Massachusetts, and was contested by D.C. United and the Los Angeles Galaxy in a rematch of the inaugural 1996 final that had been played at the same venue.

Galaxy defender Robin Fraser left the match with a broken collarbone during the opening minutes and goalkeeper Kevin Hartman collided with John Maessner at the end of the half.

It was the first MLS match to be played with a standard game clock and without a tiebreaker shootout following a rule change approved by the league days earlier.

The Galaxy blamed their performance on decisions by referee Tim Weyland and the quality of the pitch at Foxboro Stadium, which had a narrowed width and was damaged by an earlier National Football League game.

MLS announced the stadium as the host venue on October 23, 1998, and the match was scheduled three weeks later than previous editions to avoid conflicting with baseball's World Series.

[5][6] The match was played six days after a home game for the New England Patriots of the National Football League, necessitating the retention of the stadium's bleacher sections.

[24] The Galaxy hosted the first leg and led with an eighth-minute strike from defender Ezra Hendrickson, but had midfielder Simon Elliott sent off with a red card ten minutes later.

[25][26] The Galaxy defeated the Rapids 2–0 at Mile High Stadium in Denver, scoring twice in the final 15 minutes through midfielders Danny Pena and Joe Franchino, to complete a two-match sweep in the series.

[29] The Galaxy twice took the lead during the second leg at the Cotton Bowl through a brace from Carlos Hermosillo but Dallas equalized to force a tie-breaking shootout.

[30] The Galaxy clinched their place in their second MLS Cup final with a 3–1 win, having taken advantage of the Burn's weakened defense in their starting lineup due to an injury and suspension.

[38] Rongen turned to a lineup of reserves, including an inexperienced four-man defense, minor-league players, and new acquisitions to secure a playoff berth in late August.

[48] The second leg in Columbus ended in a 5–1 victory for the hosts, giving United their worst playoff defeat and forcing a third match in the series.

Roy Lassiter scored early for United in the sixth minute but the Crew responded with first-half goals from Ansil Elcock and Jeff Cunningham, and a hat-trick from Stern John in the second half.

Moreno scored in the 17th minute and was joined by a brace from Roy Lassiter on both sides of half-time, the latter coming from a bicycle kick in the penalty area.

Marco Etcheverry, who had provided three assists on the earlier goals, scored a free kick from 23 yards (21 m) with four minutes remaining to clinch a MLS Cup final berth for United.

The ABC broadcast was led by play-by-play announcer Phil Schoen and color commentator Ty Keough, who were joined by studio host Rob Stone.

[60][61] Although the shootout change was planned to take effect at the start of the 2000 season,[62] after consulting with coaches Schmid and Rongen, league commissioner Don Garber announced the revised clock and tiebreaker would be used at MLS Cup 1999.

[59][64] Approximately 5,000 D.C. United fans, including the club's two largest supporters groups Barra Brava and Screaming Eagles, traveled to the match.

[65][66] The field was described as "badly scarred" due to a National Football League game at the stadium earlier in the week, which also caused the pitch to be narrowed to 68 yards (62 m).

[71] United took the lead in the 19th minute on a long throw-in from Marco Etcheverry that was misplayed by Jolley and fell to Lassiter, whose shot was saved by Kevin Hartman.

[73][74] The Galaxy and United traded more scoring chances as the first half ended; play stopped in the 43rd minute after Maessner, who was clearing the ball, kneed Harman in the head.

[75][76] Hartman returned to the match and stopped a 22-yard (20 m) volley from United defender Jeff Agoos at the beginning of stoppage time, which Weyland set at four minutes.

[72][76] United looked to extend their lead in the second half but were unable to convert an early chance in the 47th minute as Lassiter headed a cross from Agoos wide of the goal.

[75] Commissioner Don Garber stated he thought it was "terrific to have a dominant team" when asked whether United's performance would hurt the league but added he would "love some balance".

[84][85] After the match, Hartman attributed his miscue on the second goal to the poor condition of the pitch, which United defender Jeff Agoos also criticized.