[2] The league engaged skater/speedskater Susan (Sabin) Schwartz to train and coach the 66 skaters and eventually Windy City began holding bouting events in July 2005, and by the end of the year was regularly drawing 2,000 fans to games at Chicago's Congress Theater, attracting the largest audience flat-track derby had yet seen at the time.

[4] That first season the league used a smaller than regulation-sized track due to limitations at their venue - they literally skated in the orchestra pit at the Congress Theater[5] - and moved to Cicero Stadium in early 2006 for a proper-sized space.

[8][9] On August 25, 2007, Chicago attorney Tahirah Johnson, skating as "Tequila Mockingbird" for The Fury, was injured in the most serious accident of the current roller derby revival.

[11][12] Windy City has a four-team home league, comprising the Double Crossers, the Fury, Hell's Belles and the Manic Attackers.

[21] In November Windy City hosted the WFTDA Championships,[22] dubbed the "Uproar on the Lakeshore", with a weekend attendance of 8,815 at the UIC Pavilion.

[24] Windy won their third straight North Central Regional in 2011 by defeating Minnesota, 123-100,[25] and again fell in the quarterfinals at Champs, this time 112-95 to the Kansas City Roller Warriors.

[29] The tie (later upheld upon review by the WFTDA)[30] resulted from a scorekeeping correction made well after the end of play, avoiding a potential overtime jam[31] which ordinarily would have settled the score.

[32] After winning their opening round match against the Philly Roller Girls, Windy lost their quarterfinal to Bay Area Derby, 230-135.

[36][37] In October Windy City missed WFTDA Championships for the first time with a ninth-place finish at the Omaha Division 1 Playoff, ending with a victory over Toronto Roller Derby.

[41] In 2018 at the WFTDA Playoff in Atlanta, Windy City finished out of the medals, ending their weekend with a consolation round loss, 213-185 to Ann Arbor Roller Derby.