Well, we had the Atlanta Braves win the Series over the Houston Astros a few days ago. Around that time, the always informative Kevin Glew mentioned the first Canadian to play in the World Series as we know it now (1903-) was John O'Neill in 1906.
That piqued my interest on how many Canadians played in the World Series. Fortunately, the wonderful people at the Canadian Baseball Hall of Fame did a lot of the legwork for me.
So, this list is from the Canadian Hall. Check out their site on the link above.
So as mentioned, John O'Neill was the first, playing for the White Sox in 1906
Next player to play in the Series is Jimmy Archer in 1907 for Detroit and 1910 for the Cubs.
George Gibson played and was on the winning 1909 Pirates
Larry McLean played in the 1913 Series for the Giants
Jack Graney was part of the winning Cleveland team in 1920
George Selkirk played in 6 World Series with the Yankees. He was part of five winning teams
1936, 1937, 1938, 1939, and 1941. He was on the losing end of 1942.
Johnny Rutherford played for the Dodgers in 1952
Ron Taylor is one of two Canadians to play in the World Series for two teams. He's the only one to win a Series with two teams. He was part of St Louis in 1964, and the Mets in 1969
John Hiller played in the Series for Detroit in 1968, helping them win.
Reggie Cleveland played in the World Series for Boston in 1975
Rob Butler was a part of the Series winning Toronto Blue Jays in 1993
Next we have to go to 2004 to find a Canadian in the Series.
Larry Walker was part of the losing St Louis Cardinals
Jeff Francis played in the Series for the Colorado Rockies in 2007, part of a losing effort.
Eric Gagne pitched in the 2007 World Series, helping Boston win.
Matt Stairs made two consecutive trips to the Series, winning in 2008 and losing in 2009 for Philadelphia
Next we have 2013. John Axford was part of the losing Cardinals team
While Ryan Dempster was part of the winning 2013 Boston Red Sox
Now, this year we had the Braves win. There are three Canadian connections on the team.
First Alex Anthopolous is Canadian.
Mike Soroka was injured the entire season, otherwise he'd be on this list.
Freddie Freeman is Canadian tangentally, as his parents are both from Ontario. Apparently, his mother was from Peterborough.