Curtis Joseph never made a Cup final, but he did make two Conference Finals. Since they are both losses, I'll also include the previous series he won.
1999 Playoffs
Penguins beat Leafs 2-0
Shots: Leafs 20 Penguins 19
Leafs 0 Penguins 1
The Leader-Post· May 8, 1999
The Penguins would have been up by two or three goals at the end of the first period, but not for some superb saves by Joseph. Barrasso's shutout was his first in the playoffs in three years.
Leafs win 4-2
Shots: Leafs 25 Penguins 27
Leafs 1 Penguins 1
The Leader-Post· May 10, 1999
Kip Miller and German Titov beat Curtis Joseph, who was at his acrobatic best.
Penguins win 4-3
Shots: Leafs 29 Penguins 21
Leafs 1 Penguins 2
The Leader-Post· May 12, 1999
The Penguins got only three shots in the third period, but scored on two in a game decided by a pair of frantic flurries.
Asked if it was unusual Pittsburgh won with so few shots in the pivotal period, Joseph said: "You'd think so, but this is a funny game."
Leafs win 3-2 in OT
Shots: Leafs 30 Penguins 14
Leafs 2 Penguins 2
Pittsburgh Post-Gazette · May 14, 1999
There is little more at stake for Jaromir Jagr and Curtis Joseph. Jagr, the best player in the world during the NHL's regular season, is trying to prove he can carry his team when the lights are shining brightest.
Joseph knows what that's like. People in Toronto will tell you that you can keep Dominik Hasek, they'll take Joseph. He might have been the best goaltender in the league in the regular season, but these are the playoffs. He has never gone beyond the second round.
[Joseph] did more for the Maple Leafs than Jagr did for the Penguins. Toronto won a thriller, 3-2, in OT.
Leafs win 4-1
Shots: Leafs 20 Penguins 16
Leafs 3 Penguins 2
Beaver Country Times · May 16, 1999
If they're going to be so picky as far as firing the puck at Curtis Joseph, they're going to have to do a better job of screening the Maple Leafs' goalie.
Leafs win 4-3 in OT
Shots: Leafs 30 Penguins 28
Leafs 4 Penguins 2
Beaver Country Times · May 18, 1999
"Joseph played excellent all season long," Jagr said. "He's a great goalie. If you want to win a championship, you have to have a lot of skill players and a very good goalie. That is what they have right now."
There was better goaltending from both Toronto's Curtis Joseph and Pittsburgh's embattled Tom Barrasso than the two teams coming for seven goals would suggest.
Good series overall. Joseph is the most praised Leaf and second most praised player after Jagr. Leafs do a good job of preventing shots.
Sabres beat Leafs 5-4
Shots: Leafs 32 Sabres 21
Leafs 0 Sabres 1
Beaver Country Times · May 24, 1999
The series was supposed to be a battle of two of the best goalies in the world - Hasek and Curtis Joseph of the Maple Leafs. Instead, it was a veritable rookie [Roloson] against Joseph, and it was the 10-year veteran who turned in the shaky game.
Joseph, who had allowed just 25 goals in 12 games and stopped 291 of 313 shots [0.930%) in leading the Maple Leafs past Philadelphia and Pittsburgh, allowed the five goals on Buffalo's first 19 shots.
Leafs beat Sabres 6-3
Shots: Leafs 28 Sabres 33
Leafs 1 Sabres 1
The Day · May 26, 1999
It didn't take the Buffalo Sabres long to find out the real Curtis Joseph was back in the Toronto goal Tuesday night. Midway through the first period, Stu Barnes broke in alone on Joseph, in a bid to score the game's first goal. But Joseph smothered the hard shot, and less than two minutes later the Leafs had a 2-0 lead.
"You want to make those saves early," said Joseph, who finished with 30 stops. "You want to give your team confidence."
Sabres win 4-2. Hasek returns.
Shots: Leafs 26 Sabres 24
Leafs 1 Sabres 2
Observer-Reporter · May 28, 1999
For a change, Dominik Hasek didn't dominate. This time his Buffalo Sabres teammates made it so he didn't have to.
After Joseph made a terrific pad save on Brian Holzinger in front, Barnes chopped in the rebound before the defense could react.
Sabres win 5-2. Joseph pulled after two periods
Shots: Leafs 33 Sabres 32
Leafs 1 Sabres 3
The Vindicator · May 30, 1999
Buffalo put the game out of reach when its relentless attack forced the Toronto defence into mistake after mistake in front of beleaguered goalie Curtis Joseph.
The loss was another harsh setback for Joseph, who often spectacular goaltending during his first season with the Maple Leafs had been credited for allowing the younger players on the team to develop more quickly.
He was always there to atone for their mistakes, but not on this night.
Sabres win 4-2
Shots: Leafs 24 Sabres 22
Leafs 1 Sabres 4
The Leader-Post· Jun 1, 1999
The Buffalo Sabres have proved, once and for all they contend, that they are not a bunch of nobodies riding on Dominik Hasek's goaltending pads.
Toronto needed goaltender Curtis Joseph to steal them a game in the series, but it never happened.
Well, the Sabres miss Hasek for two games and still win the series 4-1. As the last line said, Toronto needed Joseph to steal them a game and he didn't.
2002 Playoffs
Sens beat Leafs 5-0
Shots: Leafs 27 Sens 33
Leafs 0 Sens 1
Beaver Country Times · May 5, 2002
You could see the writing on the wall for Curtis Joseph in Game 11. After giving up five goals in the first 30 minutes of the game, the Maple Leafs goalie was booed by fans and left in the game by coach Pat Quinn. Joseph has a broken glove hand, was playing on one day's rest and needed a mental and physical break. Yet, Quinn just left him in the game. That kind of treatment will ensure Joseph will not even consider the Leafs when he becomes a free agent July 1.
While many say Joseph's poor play is hurting his value on the free-agent market, he actually might be helping himself. The 35-year-old goalie is gutting it out to try to help his team win. That's a great sign for any team seeking his services.
Leafs beat Sens 3-2 in triple OT
Shots: Leafs 42 Sens 56
Leafs 1 Sens 1
The Leader-Post · May 6, 2002
Anybody wondering if Curtis Joseph lost his bite should check out the teeth marks on the Senators. There are 54 of them - as in Joseph saves during the Maple Leafs' 3-2 overtime victory.
It was Joseph's finest postseason performance of the spring. He'd be un-Cujo-like ordinary. Yet, he retained his composure.
"We hung him out to dry int he first game," Shane Corson said of Joseph. "He deserved more than that because he's done such great job for us all year."
Sens win 3-2
Shots: Leafs 28 Sens 29
Leafs 1 Sens 2
The Leader-Post · May 7, 2002
Coach and GM Pat Quinn said "I don't look at the two late goals as giving us confidence [Leafs were down 3-0]. I didn't like the way we were playing and Curtis Joseph gave us a chance."
Leafs win 2-1
Shots: Leafs 24 Sens 25
Leafs 2 Sens 2
The Leader-Post · May 9, 2002
Joseph made several excellent stops for the Leafs and finished with 24 saves.
Sens win 4-2
Shots: Leafs 28 Sens 21
Leafs 2 Sens 3
No relevant comments. Joseph has an .850SV%
Leafs win 4-3
Shots: Leafs 19 Sens 23
Leafs 3 Sens 3
The Leader-Post · May 14, 2002
Goaltender Curtis Joseph, who returned from a broken hand shortly before the playoffs, has looked ordinary at various junctures during the playoffs. The criticism of Joseph reached a nadir when he was referred to as "Joe Sieve" in a scathing newspaper headline. Joseph responded with one of his finest games of the season.
Leafs win 3-0
Shots: Leafs 27 Sens 19
Leafs 4 Sens 3
The Leader-Post · May 15, 2002
Ottawa had the majority of the good scoring chances in the scoreless first period, but Joseph was outstanding.
Alexander Mogilny's two goals, one by Bryan McCabe, Curtis Joseph's goaltending and heroic defensive shot-blocking earned the Leafs a 3-0 victory.
Joseph, who has played progressively better each week...
Joseph registered the 14th - and certainly easiest - playoff shutout of his fine NHL career.
The puck seldom ended up anywhere near Joseph.
Leafs beat Hurricanes 2-1
Shots: Leafs 24 Hurricanes 32
Leafs 1 Hurricanes 0
The Leader-Post · May 17, 2002
Alexander Mogilny and Jonas Hoglund scored and Curtis Joseph turned away 31 shots and Toronto ruined Carolina's first appearance in the Eastern Conference Finals.
Peppering Joseph for 15 shots in the opening 20 minutes.
Carolina wins 2-1 in OT
Shots: Leafs 27 Hurricanes 33
Leafs 1 Hurricanes 1
No relevant comments
Carolina wins 2-1 in OT
Shots: Leafs 21 Hurricanes 17 (oof)
Leafs 1 Hurricanes 2
The Leader-Post · May 22, 2002
Carolina managed only 15 shots on goal in regulation time, but they got the only one that mattered in overtime.
Hurricanes win 3-0
Shots: Leafs 31 Hurricanes 15
Leafs 1 Hurricanes 3
No relevant comments
Leafs win 1-0
Shots: Leafs 19 Hurricanes 27
Leafs 2 Hurricanes 3
The Leader-Post · May 27, 2002
Joseph was at his best in the third period when he stopped 15 shots as the Hurricanes dominated the play. Perhaps his finest save of the night came with about three minutes to play when he made a spectacular shoulder stop on Jeff O'Neill.
The BBC line of Brind'Amour, Battaglia and Cole combined for 14 of Carolinas' first 30 goals int eh playoffs, but hasn't put one by Joseph.
Hurricanes win 2-1 in OT
Shots: Leafs 36 Hurricanes 35
Leafs 2 Hurricanes 4
The Leader-Post · May 29, 2002
"Arturs Irbe made the difference in this series and got us to the finals," said Carolina GM Jim Rutherford. Toronto's Curtis Joseph was outstanding, too. Both goalies played unbelievably well, but it's Carolina advancing.
A good, not great run. Back-to-back losses to Carolina where they don't hit 20 shots hurts. Getting cleanly outplayed by Irbe hurts. The Leafs media is all over Joseph and it sounds like his hand was never close to game-ready.
Overall, definitely get the picture of an inconsistent goalie with a good, not great team in front of him. I don't think he ever collapses in the losses, but he gets thoroughly outplayed by the opposing goalie both times.