Roy McGiffen played amateur hockey from age 15 with the Coldwater Hockey Club, moving from there to Toronto Simcoe, Toronto Amateur Athletic Club and back to Toronto Simcoe for 1909–10. He played the 1911–12 season for Cleveland of the United States Amateur Hockey Association, before turning professional with the Toronto Blueshirts in 1912–13. He played three seasons with the Blueshirts before retiring after the 1914–15 season.\n', '

In the 1914 Stanley Cup challenge of Victoria against the Blueshirts, McGiffen scored the game-winning goal of game two. That season, he led the league in penalty fines of $116.\n', '

In a 17 February 1915 regular-season game against the Ottawa Senators, McGiffen became involved in a fight with Art Ross that ended with both players being arrested by Toronto police. After spending the night in jail, both players were fined $1. McGiffen lost a coin toss with Ross and paid both fines. The referee of the match Cooper Smeaton wanted McGiffin barred from the league, denouncing him as a rough player.\n', '

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