During this time he frequently played on Montreal's top line with Jean Beliveau and Bernie Geoffrion.

[1] Olmstead was claimed in the 1958 NHL Intra-League Draft by the Toronto Maple Leafs, and played there until his retirement in 1962.

In his first year, Olmstead and the Moose Jaw Canucks challenged for the Memorial Cup, after finishing the playoffs with a 15–1 record.

He played another season in Moose Jaw, before being assigned to the Kansas City Pla-Mors of the United States Hockey League (USHL) by the Chicago Black Hawks.

[2] Olmstead played three full seasons for Kansas City, and part of another, later in 1950, for the Milwaukee Sea Gulls.

[4] The same season, Olmstead made his NHL debut, called up after scoring 33 goals and 44 assists, for 77 points, in 52 games with the Pla-Mors.

Olmstead played the entire following season for the Black Hawks, appearing in 70 games and scoring 20 goals.

[3] On December 2, 1950, Olmstead, with Vic Stasiuk, was traded to the Detroit Red Wings, in exchange for Lee Fogolin and Steve Black.

[5] Olmstead would never leave the NHL until his retirement in 1962, playing 39 games that season on a line with Maurice Richard and Elmer Lach, scoring 38 points.

[2] In the 1954–55 season, Olmstead led the league in assists, with 48, as Montreal lost another Stanley Cup Finals to Detroit.

[4] The same season, the Leafs went on a long winning streak in order to qualify for the playoffs, but they lost to the Canadiens in the finals.

[3] Following his fifth Stanley Cup win, with Toronto, the New York Rangers claimed Olmstead in the Intra-League Draft on June 4, 1962.

[8] Known as "Dirty Bertie" because of his physical playing style, Olmstead was a power forward, making hard hits and winning battles in the corners.