Boston Bruins icon Cecil "Tiny" Thompson was the first to win 250, hitting the mark in 1938-39. He won 284 in his career.
Safe for decades -- and possibly forever -- atop the list is NHL leader Martin Brodeur, his 691 wins are 140 clear of the 551 by second-ranked Roy. Nearest to Brodeur among active goalies is Roberto Luongo of the Florida Panthers, whose 446 wins rank him sixth, one behind the late Terry Sawchuk.
Plante won 437, ranking him seventh all-time. His 314 wins with Montreal from 1952-1963 lead the Canadiens. Roy, who played for Montreal and then the Colorado Avalanche, is next with 289 Canadiens victories, earned between 1984 and 1995. Then comes Dryden, whose 258 wins, all with the Canadiens from 1971 and 1979, are the 47th most in League history.
Price is third on the Canadiens' list of games played with 469 (heading into Saturday 12/17), the 556 of Plante and 551 of Dryden possibly within reach next season. Price is fourth on the franchise list with 38 shutouts, trailing Hainsworth's 75, Plante's 58 and Dryden's 46, and his career 2.40 goals-against average ranks him sixth on the Canadiens among goalies having played at least 100 games.
Plante earned his 250th victory on Oct. 22, 1961 in his 435th NHL game, a 3-2 road win against the Chicago Blackhawks. Dryden, in his 381st game, won No. 250 on Jan. 27, 1979, a 3-1 home win against the Bruins. Roy's 250th win came in his 469th game, a Feb. 7, 1994 road win against the Pittsburgh Penguins.
Price's first NHL game was in Pittsburgh on Oct. 10, 2007; it came on the 22nd anniversary of Roy's first regular-season NHL start in 1985, a 23-save, 5-3 victory that came in Pittsburgh's Civic Arena, later renamed Mellon Arena.
Price turned aside six shots by Sidney Crosby in his maiden game, Crosby having been the No. 1 pick in the 2005 NHL Draft, four spots ahead of Price.
"You look at that (Penguins) lineup and you go, 'Whoa, that's some high-octane snipers," Price said post-game, having made 26 saves. "(But) I wasn't that nervous. We did a good job keeping everything away from me."
Dryden played his first game in the same Pittsburgh arena as Roy and Price, making 35 saves in a 5-1 Canadiens win on March 14, 1971. That came two months before Dryden anchored a Stanley Cup victory while winning the Conn Smythe Trophy as the most valuable player in the postseason.
Fifteen years later, Roy would do exactly the same with the 1985-86 Canadiens.
The Penguins didn't exist when Plante debuted in a 4-1 win at the Montreal Forum against the New York Rangers on Nov. 1, 1952, called up in emergency relief of injured Montreal goalie Gerry McNeil. Seven years later, to the night, Plante would leave the Madison Square Garden ice for stitches after being badly cut by a puck, his returning with a mask for the first time in his career changing the face of goaltending forever.
At various times during his nine-plus NHL seasons, Price has featured the airbrushed likenesses of Plante, Roy and Dryden on his mask. With Price's 250th win, the bond of the four has never been tighter, Canadiens lodge brothers of excellence no matter that they reached the milestone decades apart.