Columbus won the Supporters' Shield with the most regular season points and defeated Kansas City and the Chicago Fire in the playoffs to reach the final.

The Red Bulls finished the regular season with a losing record and were seeded into the Western Conference bracket as a wildcard, eliminating defending champions Houston and Real Salt Lake in the process.

Columbus won the game by a score of 3–1 with goals from Alejandro Moreno, Chad Marshall, and Frankie Hejduk — all assisted by Guillermo Barros Schelotto.

[12] The mayors of Columbus and New York made a ceremonial bet prior to the match, promising to exchange local foods and beer to the winning city.

[13] The Columbus Crew hired manager Sigi Schmid at the end of the 2005 season to lead a rebuilding process after the team finished at the bottom of the Eastern Conference.

[15][16] Argentine forward Guillermo Barros Schelotto was signed in April 2007 and led the team as it fell several points short of playoff qualification in the final weeks of the season.

[22][23] The Crew played against the Kansas City Wizards in the Eastern Conference Semifinals, drawing 1–1 in the first away leg on a goal scored by substitute Steven Lenhart in stoppage time.

[29] The team began the 2008 season, their second under the Red Bull brand,[30] with Colombian manager Juan Carlos Osorio replacing Bruce Arena as head coach.

[32][33] The team's other star striker, Juan Pablo Ángel, recovered from back and hamstring injuries to lead the Red Bulls to a playoff berth on the final day of the season, finishing ahead of D.C. United with only 39 points and a losing record.

Salt Lake then hit Cepero's goalpost three times, but were unable to score an equalizer and allowed the Red Bulls to advance to their first MLS Cup final.

[45] Recording artist Colby O'Donis performed the national anthem and indie pop group Chester French headlined a pregame festival at the final.

[11] The match kicked off in sunny weather in front of 27,000 spectators, including several thousand Crew fans who re-created the "Nordecke" in the northeastern corner of the Home Depot Center.

[51][53] While the Red Bulls sought a second equalizer, including a shot by Richards that was saved by goalkeeper Will Hesmer, Columbus continued to push with attacks led by Frankie Hejduk, who sent in several crosses into the six-yard box.

[53] MLS Cup Most Valuable Player: Guillermo Barros Schelotto (Columbus Crew) Assistant referees: Greg Barkey Kermit Quisenberry Fourth official: Mark Geiger Match rules: The Crew became the fourth club to win both MLS Cup and the Supporters' Shield in the same season, following D.C. United (1997, 1999), Sporting Kansas City (2000), and Los Angeles Galaxy (2002).

[63] Both finalists qualified for the 2009–10 CONCACAF Champions League, with the winning Crew seeded directly into the group stage and runners-up Red Bulls entering in the preliminary round.