As a youth, Cumiskey played in the 1999 Quebec International Pee-Wee Hockey Tournament with a minor ice hockey team from Abbotsford, British Columbia. He later played one year of Jr.A. hockey with the Penticton Panthers of the BCHL. He was not selected in the 2001 WHL Bantam Draft, and signed as a free agent with the Kelowna Rockets in 2003.[citation needed]\n', '

Cumiskey played junior hockey for the Kelowna Rockets of the Western Hockey League for three seasons, scoring 79 points in 177 games. He was drafted by the Colorado Avalanche in the seventh round of the 2005 NHL Entry Draft, 222nd overall, after his second junior season.[citation needed]\n', '

Cumiskey played most of the 2006–07 season for the Albany River Rats of the American Hockey League but appeared in nine games for the Avalanche. His first career NHL goal was the only goal in regulation for the Avalanche in a 2–1 shootout win over Manny Fernandez and the Minnesota Wild on January 6, 2007. During the next two seasons, Cumiskey split time between the Lake Erie Monsters of the AHL and the Avalanche; however, he was sidelined by injuries for a significant amount of time in both years. A groin injury caused Cumiskey to miss 17 games in the 2007–08 season, and his 2008–09 season ended early with shoulder surgery on February 18.\n', '

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