 Holmes played as an amateur for three season with the Parkdale Canoe Club of the Ontario Hockey Association (OHA) from 1908 to 1911, before joining the professional Toronto Blueshirts of the National Hockey Association (NHA) in 1912 – 13. Holmes won the first of his four Stanley Cups in 1914. Although being under contract to the Blueshirts, Holmes joined the Seattle Metropolitans of the Pacific Coast Hockey Association (PCHA) for the 1915 – 16 season, winning his second Stanley Cup (1917) in his second season with the Metropolitans. For the 1917 – 18 season, Holmes ended up playing for the Torontos (the following year renamed as the Toronto Arenas) of the National Hockey League (NHL) through a series of loans by other teams. Holmes won his third Stanley Cup in his only full season with the Torontos. After playing two games in the 1918-19 season for the Toronto Arenas, Holmes would be recalled by the Metropolitans. Holmes played for the Metropolitans for the next six seasons, until the team folded. In the 1924 – 25 season, Holmes joined the Victoria Cougars of the West Coast Hockey League (WCHL / WHL). Holmes played for the Cougars for two seasons, winning the Stanley Cup for his fourth and last time. After the WCHL / WHL league folded, Holmes joined the Detroit Cougars of the NHL, playing with the Cougars for two seasons before retiring.
