On October 12, 1999, the Revolution named Sunil Gulati managing director of Kraft Soccer and appointed Brian O’Donovan as chief operating officer.
[2] Following the dismissal of Walter Zenga on September 30, the Revolution appointed Fernando Clavijo as their fourth-ever manager (following Steve Nicol's interim stay at the end of the 1999 season).
[7] In the 2000 MLS SuperDraft, Revolution selected Rusty Pierce, Shaker Asad, Fabio Zúñiga, Bo Oshoniyi, Adam Eyre, and Tom Hardy.
[1] The season opened on March 18 with a 1–1 draw away to the Miami Fusion, courtesy of an Imad Baba 80th minute equalizing goal.
[6] In July, the Revolution acquired U.S. International Eric Wynalda and future draft considerations from the Miami Fusion in exchange for defender Ivan McKinley.
[12] The Revolution made history in the 2000 U.S. Open Cup, becoming the first-ever MLS team to lose to an amateur club, when they were defeated in the second round at home by the Mid Michigan Bucks 1-0.
[14] In the Revolution's second-ever playoff campaign, the club squared off against "Central Division" champion and overall 2nd-seed Chicago Fire in a best-of-three series.