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Phil Housely and Dale Hunter come to mind glancing at the all time games leaders but I'm pretty young so there may be some players from early in the 20th century I do not know about who didn't win the cup. The record had been held by Dave Andreychuk, who had played 1597 regular season and 1758 total games without winning, until he captained the Tampa Bay Lightning to their '04 Cup win. At this point, Housley is the leader with 1495 regular season games. Scott Mellanby leads among active players with 1362 regular season games.

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Q: Which NHL player participated in the most career combined regular season and playoff games without winning a Stanley Cup?
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