3 (97,98,08) All with Detroit. Starting goaltender in 98 and 08. Tho he was the No. 1 goalie during the 96-97 regular season, playing 47 of 82 games, Vernon got the start for the playoffs. Osgood missed out on the 02 Cup when he was with the Islanders.
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3, at least until tonight (he'll win his 4th Cup tonight, 6/12/09). Osgood is one of the Top 25 goalies to ever play in the NHL, and one of the most underrated. Rodney Dangerfield would have a field day with some of the unfair comments made about Osgood.
Edit - The respondent jumped the gun as the red wings did not win the Stanley cup in 2009. Also although Osgood was a member of "3" Stanley cup winning teams he was the starting goal tender for just 2 of them ('98 and '08) . In 1997 he watched Mike Vernon win from the bench. Osgood's career will forever be marred by the fact that he had some of the best teams ever assembled in the NHL in front of him during most of his playing career, many people feel we will not be elected to the hall of fame and that comments of him being underrated are somewhat exaggerated. Osgood is a very capable goalie and was always just enough to put the redwings over the top but he does not make the list of top 25 goalies ever, unless that list is put together in Detroit.
3 cups (97, 98, 08)
started two of those years (98, 08)
vernon started in 97
osgood was not with the red wings when they won in 02