Clare "Rags" Raglan, although born in Pembroke, grew up in Toronto. He attended Runnymede Collegiate Institute while playing junior hockey for the Toronto Marlboros and other area teams. Raglan was lured to the Quebec Senior league by the Quebec Aces in 1947. Under coach Punch Imlach the team pulled off an upset of the Montreal Royals in the playoffs the following spring. Clare remained with the team for another season before turning pro.
The Detroit Red Wings signed Raglan to a contract in 1949 and shipped him off to Indianapolis. The Capitals became the first club in American Hockey League history to sweep their way to the Calder Cup. The next season saw his NHL debut when Marcel Pronovost's demotion opened a spot on the Detroit roster. "Rags" recorded his first point, an assist, when the Red Wings traveled to New York to face the Rangers on December 6, 1950. A little over a week later he collected his first goal as he tipped in Jim McFadden's rebound past Boston goaltender Jack Gelineau.
Raglan traded places with Marcel Pronovost the following February and finished out the season in Indianapolis. In the off-sea son Detroit traded him to the woeful Chicago Black Hawks. Over the next two seasons Clare split his time between the Hawks and their minor league affiliates in St. Louis and Edmonton before returning to the Quebec league in 1953. Clare played the next two seasons in the AHL with Buffalo. In his first season with the Bisons the team went to the finals before losing to Pittsburgh. Raglan departed for the west coast for the 1956-57 season. Eighteen games into the campaign with the Vancouver Maroons Clare Raglan' s season ended.
The defenseman suffered a double fracture of his right leg in the November 20, 1956 game against Victoria. He had tried to throw a heavy check against Wayne Brown and suffered the breaks when the pair fell to the ice. Years later Raglan would point to that game as the crucial game in ending his career. Before the end of his playing days Clare Raglan became a world champion with the Belleville McFarlands at the 1959 World Hockey Championships in Prague.