 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 . 
