When the Vegas Golden Knights eliminated the Winnipeg Jets in Game 5 of the Western Conference Final on Sunday, Fleury earned his 74th win in the Stanley Cup Playoffs, tying Osgood for eighth in NHL history.
Fleury is 12-3 with a 1.68 goals-against average, .947 save percentage and four shutouts entering the Stanley Cup Final, which the Golden Knights will play in beginning Monday against the Tampa Bay Lightning or Washington Capitals, who play Game 7 of the Eastern Conference Final on Wednesday (8 p.m. ET; NBCSN, CBC, SN1, TVAS).
[RELATED: Gallant keeps mood light as Golden Knights await Cup Final opponent]
"He's been absolutely phenomenal," Osgood said. "I think this is the best I've ever seen him play in the playoffs. When needed most, he's at his best each and every time. That's what I'm most impressed with."
At this point in his career, Fleury, 33, has a lot in common with Osgood, 45, now retired and a TV analyst in Detroit:
* Fleury has 404 regular-season wins, 11th in NHL history, three more than Osgood. Each earned most of his wins with a marquee team at the time -- Fleury 375 with the Penguins, Osgood 317 with the Red Wings. Neither has won the Vezina Trophy as the NHL's best goaltender.
* Each has three Cup rings. Osgood won two as a starter (1998, 2008), one as a backup (1997). Fleury won one as a starter (2009), one as both (2017) and one as a backup (2016). Osgood won his first Cup as a starter at 25; Fleury won his first as a starter at 24. Osgood won his third Cup at 35; Fleury won his third at 32.
* Each lost his job. Osgood was claimed by the New York Islanders in the Waiver Draft on Sept. 28, 2001, after the Red Wings acquired Dominik Hasek. Fleury was claimed by the Golden Knights in the NHL Expansion Draft on June 21, 2017, because the Penguins wanted to protect Matt Murray.
* Each came back with the best playoffs of his career in his 30s. After bouncing from the Islanders to the St. Louis Blues to the Red Wings again, Osgood was outstanding in the 2008 and 2009 playoffs. In 2008, at 35, he went 14-4 with a 1.55 GAA, the lowest of his career; a .930 save percentage, the highest of his career; and three shutouts, the most of his career. In 2009, at 36, he went 15-8 with a 2.01 GAA, a .926 save percentage and two shutouts. Now Fleury has the best numbers of his career.
Video: Is Fleury the front-runner for the Conn Smythe?
"As your career goes along and you're in one place, sometimes change is good," Osgood said. "Murray was there [in Pittsburgh]. He'd won a Cup. Murray's a great teammate, but at the same time, I think the change of scenery was great for [Fleury].
"Not that you'd ever think this was going to happen on an expansion team. No way. But he's the centerpiece of that. You've got a goalie that's won the Cup. Put him on that team, that's the difference-maker. He's proven that all year. … Not only that, he's a great guy. He does everything the right way, and now he's getting rewarded for it."
Osgood said he thought if Fleury hadn't sustained a concussion and missed two months of the regular season, he probably would have won the Vezina. Among goaltenders who played at least 45 games, Fleury tied with Antti Raanta of the Arizona Coyotes for first in goals-against average (2.24) and tied with Pekka Rinne of the Nashville Predators for second in save percentage (.927) behind Raanta (.930).
"It's not easy, and I've done it," Osgood said. "You lose your job. You're not playing. You have to bring up these young guys, because you're a good teammate. I see the difference in [Vegas backup Malcolm] Subban when he's in there too, the way he plays. The trickle-down effect for having a goalie like that is so great on so many different levels, that people don't even notice. It's unbelievable to me, from Subban to the players to when times get tough and you know he's going to play a great game."
One more parallel: Fleury's goaltending coach in Vegas, David Prior, was once Osgood's goaltending coach in Detroit. Prior teaches his goaltenders to be aggressive and not give ground easily, so the shooters have less net to target. But Prior's goaltenders need to be athletic, and his teams need to be able to cover the flanks.
Video: VGK@WPG, Gm5: Fleury on series, going to Cup Final
"I'm glad to see David Prior still coaches like that, because a lot of guys tend to put too much stuff in these guys' heads and over-coach them," Osgood said. "It's already a difficult position. It's the most unpredictable position you can play. Things never happen like you think, so you have to react.
"Fleury, to me, is one of the best reaction goalies there is now in the National Hockey League. He still makes the blocking easy saves, but he lets his athleticism come out when it has to. Like Jonathan Quick [of the Los Angeles Kings], but a little more calm."
Osgood has a strong case for the Hockey Hall of Fame. Of the nine retired goaltenders ahead of him in regular-season wins, two are not in the Hall. One is Martin Brodeur, a lock, and the other is Curtis Joseph, who never won the Cup. Of the seven retired goaltenders ahead of him in playoff wins, two are not in the Hall. One is Brodeur. The other is Mike Vernon, who won 77 playoff games; two Cup rings, with the Calgary Flames in 1989 and the Red Wings in '97; and the Conn Smythe Trophy as most valuable player in the playoffs in '97.
What if Osgood had defeated Fleury again in 2009? It came down to Game 7 of the Final. But how much would one more win -- giving him a fourth ring, his third as a starter -- have helped his case?
What if Fleury wins a fourth ring -- his second as a full-time starter, his third as a huge contributor -- and does it with an expansion team? What if he wins the Conn Smythe, too? What if he keeps adding to his resume in the future?
Osgood said he could see Fleury playing at a high level for years.
"I just think the older you get, the game slows down even more," Osgood said. "You have less panic in your game. You tend not to overreact when things don't go well. He's always been like that, but I think even more so now. …
"He's relaxed, but he's a competitor. And I do think he had something to prove when he went there. He's been phenomenal. Right now in the playoffs there's not another goalie I'd want in the net after a team loses than him, without a doubt, because he doesn't change. I think that Fleury's Fleury. He's one of the best goalies to ever play. But he brings that confidence to the room."