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Ryan was the third-overall draft pick in the major junior Western Hockey League bantam draft, by the Tri-City Americans. Ryan was named the Western Hockey League Rookie of the Year in ’93 and Most Improved Player in ‘94. The following year, he won the WHL's Plus-Minus Award, was named Most Spirited Player, and claimed the fourth overall ranking in league scoring (50 goals, 60 assists).

Ryan has played Newfoundland senior hockey with the St. John’s Capitals and the Clarenville Caribous, who lost the 2014 Allan Cup final to the Dundas Real McCoys in overtime. He played with his hometown Mount Pearl Blades for two seasons, missing the playoffs both years. In 2006 he was named Top Scorer for the Avalon East League and the Newfoundland Provincial League; in 2007 he claimed the title of MVP and Avalon East Top Scorer. In 2008, he played with the Bentley Generals of the Alberta Senior Hockey League, winning a silver medal at the Allan Cup, and was named Top Scorer. Ryan is an avid baseball player in the summers, suiting up for the Mount Pearl Knights of the St John's men's baseball league. He also swims laps at the local swimming hole behind Agnes Pratt Mercy Home in Rennies River.

In 2017, Ryan unsuccessfully ran for city council in Mount Pearl.

Ryan, who has a bachelor of arts degree (Folklore/English), released his first book, "Tales of a First Round Nothing" in May 2014, which was well-received by critics. He is now also trying his hand at stand-up comedy and performed his second show to good reviews opening for Gerry Dee at the General Motors Centre in Oshawa, Ontario on April 22, 2016.

Ryan works in the film industry and has appeared on several episodes of the hit CBC television program Republic of Doyle, playing small roles. He has also played himself in the OLN's "Road Hockey Rumble", and played Zombie #22 in Zack Snyder's "Dawn of the Dead" (2004). In addition to playing "British Soldier #1" (Episode 1) - (the first on-screen casualty in the Netflix/Discovery Channel television series Frontier, starring Jason Momoa in the lead role), in 2017 Ryan also had small roles in Frontier Season 2, Little Dog (CBC), Caught (CBC), Schitt's Creek, and various short films. He wrote and played the lead role in a short film called "A Stand In" due in 2018.

In 2003, 2005, 2007, 2009, 2011, and 2013 Ryan represented Canada at the ISBHF ball hockey tournament in Switzerland, Pittsburgh, Germany, Czech Republic, Slovakia, and Canada respectively. He led the team to a gold medal in ’03 and ’07, won a silver in 2011, and won a bronze medal representing Canada again at the 2013 Worlds in St John’s, NL, his hometown. In 2011 in Bratislava, Slovakia, Ryan was Canada’s leading scorer. He also has two national ball hockey championships to his credit (Montreal Black Knights, 2008, and Newfoundland Black Horse, 2010). In 2016, he reached the provincial ball hockey championship finals. In 2018, his team, Colonial Auto Parts from St. John’s, won the 2018 Canadian men’s masters championship, and his other team, Black Horse, took silver in the national ball hockey championships in the senior men’s A competition.

Despite his high draft ranking, Ryan played only 8 games in the NHL over parts of three seasons, all spent with Montreal, failing to register a single point and suffering a career-ending ankle injury in 2001, ending his chances at returning to the big leagues. Due to such a short NHL career, Ryan is often considered a draft bust. The majority of his career was spent in the minor professional hockey leagues. He signed in St John's in 1999–2000 to play for his hometown Maple Leafs, but was never signed by Toronto themselves due to a contractual conflict with the Canadiens. In 2000, Ryan won the St. John's Maple Leafs Humanitarian of the Year Award; in 2003 he led the Orlando Seals with playoff goals (8) to help them win the league championship.

Ryan was selected 8th overall, in the 1995 NHL Entry Draft. He was selected as the 1st choice of the Montreal Canadiens. His hockey career continued with the Fredericton Canadiens where he was named Rookie of the Year in 1998, claimed second in goals (21) and led the league in fights (34).

In 1991, at 14 years of age, Ryan was invited to play Junior “A” hockey for the Quesnel Millionaires in BC for two years, where he won the Top Scorer Award and was selected as a member of the Rocky Mountain League All Star Team.

As a youth, Ryan played in the 1990 and 1991 Quebec International Pee-Wee Hockey Tournaments with a minor ice hockey team from Mount Pearl.

Terrence William James Ryan (born January 14, 1977) is a Canadian retired professional ice hockey player. He was drafted by the Montreal Canadiens eighth overall in the 1995 NHL Entry Draft and played eight games with the organization between 1996 and 1999.