Cheveldae began his junior ice hockey playing career in the 1985–86 WHL season with the Saskatoon Blades. Cheveldae was selected in the 4th round (64th Overall) by the Detroit Red Wings in the 1986 NHL Entry Draft. Cheveldae remained with the Blades until the end of the 1987–88 season before leaving for the professional ranks.\n', '

For the 1988–89 season, Cheveldae went to the Red Wings\' minor league affiliate, the Adirondack Red Wings, in the American Hockey League. His level of play earned him a call up to the NHL, where he served two games in net for the Red Wings, and made him the fourth goaltender on the Red Wings roster behind Greg Stefan, Glen Hanlon and Sam St. Laurent.\n', "

While Detroit's goaltending lineup would remain the same for the 1990–91 season, Cheveldae ascended the depth chart, going from goaltending in the AHL to being in Detroit's goaltending tandem with Hanlon, as Stefan suffered career ending injuries while St. Laurent never ascended beyond the role of a third goaltender at the NHL level despite his minor league success.\n", "

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