Dwayne De Rosario became the first Canadian winner of the Trophy in 2009 after scoring three goals in a 6–1 Toronto FC victory over Montreal in the final game of that year's tournament.[2] De Rosario became the first repeat winner in 2010.[3]
Joao Plata, an Ecuadorian Forward/Winger succeeded his former short-lived teammate and captain the following year after scoring the series-tying goal and then assisting on the championship winner in the second leg of the final, becoming the first South American trophy winner in 2011.[1][4]
Toronto FC's Ryan Johnson claimed the 2012 title scoring two of the club's four goals over the four matches.[5]
Montreal Impact's Justin Mapp was awarded the trophy in 2013 becoming the first non Toronto FC player since 2008, and the first winner of the MLS-version of Montreal.[6] Mapp became the second repeat winner during the 2014 tournament.[7]
Russell Teibert became the first Vancouver Whitecaps player to win the award in 2015.[8]