The Trillium Cup was instituted in
2008, the second season of Toronto FC's play in
Major League Soccer (MLS). The inaugural game of the Trillium Cup was played on March 29, 2008, at
Columbus Crew Stadium. The initial rivalry between the Trillium teams was supported by the mayors of the respective cities. In 2008,
Mayor Michael B. Coleman of
Columbus and Mayor
David Miller of Toronto started
a small wager on their respective team for the first installment of the Trillium Cup – the mayor of the losing team was required to wear the winning team's jersey. The rivalry became more intense when Toronto FC fans bought 2,500 tickets to the inaugural game at
Columbus Crew Stadium, with buses organized for fans from Toronto heading to Columbus for the first game on March 29, 2008. The Crew won 2–0 over their new rival. The second and third meetings, at Toronto's
BMO Field, were draws; 0–0 and 1–1, respectively. The Crew claimed the inaugural Trillium Cup with a 5–2 score on points earned. In
2011, Toronto defeated Columbus 4–2, recording their first ever win against the Crew and securing their first Trillium Cup. In
2017, Toronto and Columbus met for the first time in the
MLS Cup Playoffs, in the
Eastern Conference Finals, as Toronto advanced to the
MLS Cup Final 1–0 on aggregate. ''), the provincial flower of Ontario and the state wildflower of Ohio In
2020 and
2021, COVID-19 travel restrictions imposed by the Canadian Government forced Toronto to play rivalry matches in
Pratt & Whitney Stadium in Connecticut in 2020 followed by Orlando SC's
Exploria Stadium in Orlando, Florida in 2021 where Toronto played home matches in these stadiums as the home team. This marked the first time that the rivalry matches were played on neutral ground. In 2020, Toronto won their only meeting in 2020 with Columbus 3–1 in September 2020. The next year Toronto won the first leg of the rivalry match in 2021 with a score of 2–0. Columbus Crew would later win the second leg of the rivalry in 2021 on the last rivalry match to be taken place at the
Historic Crew Stadium before the Columbus Crew moves to
Lower.com Field in July 2021. Columbus won the match 2–1. == Winners by year ==