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After playing his first 7 professional seasons in North America, Ryan left as a free agent in agreeing to a one-year deal with HC Thurgau of the second tier Swiss League, on July 6, 2018.

Ryan extended his playing career in the off-season by agreeing to a one-year deal with the Wheeling Nailers of the ECHL on August 28, 2017.

On August 10, 2016, as a free agent, Ryan opted to continue his career in the third tier ECHL, signing a one-year deal with the Cincinnati Cyclones. In the 2016–17 season, Ryan appeared in 18 games with 13 points for the Cyclones, before he was recalled and returned with the San Diego Gulls on November 29, 2016. His ECHL rights were traded to the Gulls ECHL affiliate and former club the Utah Grizzlies. After 8 games with the Gulls, Ryan was released from his try-out and was traded twice more in the ECHL between the Grizzlies and Reading Royals before ending up with the Indy Fuel on February 7, 2017.

Lingering as an unsigned free agent after the off-season, Ryan agreed to a try-out to attend the Anaheim Ducks 2015 training camp. At the conclusion of training camp, Ryan was assigned and agreed to a contract with AHL affiliate, the San Diego Gulls, on September 28, 2015.

Unsigned throughout the off-season, Ryan accepted an invitation to attend the Colorado Avalanche 2014 training camp on a professional try-out contract on September 18, 2014. He was later reassigned to AHL affiliate, the Lake Erie Monsters training camp, where he made the team's opening night roster. In the 2014–15 season, Ryan's versatility was relied upon across the line-up in appearing in a career high 73 games for a professional best of 17 assists and 29 points.

On May 26, 2011 he signed a three-year entry level contract with the Maple Leafs. During his first season with the Leafs' organization, Ryan divided his time between the team's AHL affiliate, the Toronto Marlies and their ECHL affiliate, the Reading Royals. Ryan spent the next two seasons playing exclusively for the Marlies. Following the end of the 2013–14 season, the Leafs did not make a qualifying offer to Ryan and as a result he became an unrestricted free agent on July 1, 2014.

Ryan was selected 50th overall by the Toronto Maple Leafs in the 2009 NHL Entry Draft.

Ryan played youth hockey for the USA Hockey National Team Development Program for two seasons beginning in 2007. He joined the team from the Honeybaked AAA development program. He made his Spitfires debut during the 2009-10 season. In the 2010-11 season, he recorded 58 points in 60 games played. He also collected 12 points in 18 playoff games.

Kenny Ryan (born July 10, 1991) is an American professional ice hockey right winger who is currently an unrestricted free agent. He most recently played with HC Thurgau in the Swiss League (SL). He was selected 50th overall by the Toronto Maple Leafs in the 2009 NHL Entry Draft.