Foxboro Stadium in the Boston suburb of Foxborough, Massachusetts, was announced as the venue of the inaugural MLS Cup during a league press conference on August 29, 1996.

[6][7] It also adopted an Americanized version of the game's rules, including a 35-yard (32 m) shootout to decide tied matches (for which the winners earned one point) and a countdown clock to keep time.

[15][16] The league allocated U.S. defender Jeff Agoos, U.S. midfielder John Harkes, and Bolivian forwards Marco Etcheverry and Juan Berthy Suárez to D.C. United, which signed former University of Virginia Cavaliers coach Bruce Arena as its manager in January 1996.

[21] D.C. United played in the inaugural league match against the San Jose Clash at Spartan Stadium on April 6, losing 1–0 to a goal by Eric Wynalda.

[23] In their next victory, 5–2 on May 15 against the Columbus Crew, newly added forward Steve Rammel scored the first hat-trick in league history while Etcheverry recorded three assists.

[24] D.C. went on to win three matches in a row to start June and earn the second-place spot in the Eastern Conference, trailing the Tampa Bay Mutiny by eight points.

[40] United faced the Tampa Bay Mutiny, the regular season champions with a home advantage, in the Eastern Conference Final, which was rescheduled due to stadium conflicts for both teams.

[43] D.C. United went on to win 2–1 in the second leg hosted by Tampa Bay, with goals by Richie Williams and Díaz Arce in the second half to clinch an MLS Cup appearance.

[46] The Galaxy had already acquired Mexican goalkeeper Jorge Campos, the league's first major international signing, and were also allocated American defender Dan Calichman, Salvadorian midfielder Mauricio Cienfuegos, and Ecuadorian striker Eduardo Hurtado.

[47][48] Osiander selected several experienced national team members in the general draft, including defenders Robin Fraser and Curt Onalfo, and midfielder Jorge Salcedo.

[48] The team also filled its roster by adding midfielders Greg Vanney and Chris Armas and forwards Guillermo Jara and Ante Razov from the collegiate and supplemental drafts in early March.

[57][58] Los Angeles alternated between wins and losses in early August before beginning a five-match losing streak that saw them fall to second place in the Western Conference behind the Kansas City Wiz.

[60][61] Los Angeles climbed back into first place in mid-September with victories over San Jose and twice against Dallas to finish the regular season with a 19–13 record and 49 points atop the Western Conference and second overall in MLS.

[68] San Jose striker Eric Wynalda and defender Oscar Draguicevich were ejected late during the match after each being shown two yellow cards, and were suspended for the third leg.

[68][69] The Galaxy advanced to the Western Conference Final after a 2–0 victory in the third leg, with two goals scored in the first half by Hurtado and Cienfuegos from a controversial penalty kick called against Ben Iroha.

The second leg remained tied after regulation time and overtime, with several disallowed goals called against Kansas City, and was decided in a penalty shootout from 35 yards (32 m).

[4] Phil Schoen was the play-by-play commentator, while Ty Keough and Bill McDermott provided color analysis;[4] Roger Twibell was the studio anchor and was joined by Revolution defender Alexi Lalas, who also performed the national anthem with his electric guitar.

[82][83] The weather caused league officials to consider cancellation or postponement of the MLS Cup final, but the lack of lightning allowed the match to continue as planned, kicking off with a temperature of 54 °F (12 °C).

[88] Both teams fielded most of their regular players, with the exception of Los Angeles captain Dan Calichman, who was suspended for yellow card accumulation during the playoffs.

[84][88] The Galaxy continued to have the most scoring chances early in the second half and took a 2–0 lead in the 56th minute as Chris Armas dribbled past four defenders to make a left-footed shot from 16 yards (15 m).

[28] D.C. United coach Bruce Arena brought on two midfielders, Tony Sanneh and Shawn Medved, midway through the second half who helped shift momentum in the team's favor.

[28] Los Angeles coach Lothar Osiander responded by sending on two of his own substitutes, forward Ante Razov and defender Curt Onalfo, but the team was unable to extend its lead after Cobi Jones hit the crossbar with a chipped shot in the 78th minute.

[95][96] D.C. went on to complete the "double" by winning a second trophy, the 1996 U.S. Open Cup, a week later at RFK Memorial Stadium by defeating the Rochester Raging Rhinos of the second-division A-League by a score of 3–0.