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.

[2] 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 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.