After playing his minor hockey in his hometown of Abbotsford with the Hawks minor hockey program, Cumiskey played one year of Jr.A. hockey with the Penticton Panthers of the BCHL. He was not selected in the 2001 WHL Bantam Draft, however, signed as a free agent with the Kelowna Rockets in 2003.
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.
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.
For the first time in his NHL career, Cumiskey made the opening night roster with the Avalanche at the beginning of the 2009–10 season.
In the offseason before the 2011-2012 season, Cumiskey signed a one year two-way deal with Colorado days before training camp. During the preseason Cumiskey suffered a concussion and was placed on injured reserve by Colorado. On October 7, 2011, one day before the Avs season opener, he was placed on waivers. On the following day, Cumiskey was traded to the Anaheim Ducks for Jake Newton and a conditional draft pick.
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