# 1998–99 Toronto Maple Leafs season

The 1998–99 Toronto Maple Leafs season was the franchise's 82nd season. Two moves occurred this season. First, the club moved from the Western to the Eastern Conference of the National Hockey League (NHL). Secondly, the club moved from Maple Leaf Gardens to the new Air Canada Centre. Toronto qualified for the Stanley Cup playoffs and made it to the Eastern Conference Finals before losing to the Buffalo Sabres.

## Off-season

The Toronto Maple Leafs moved from the Central Division of the Western Conference to the Northeast Division of the Eastern Conference.

## Regular season

The 1998–99 season was a tremendous improvement for the Maple Leafs over the 1997–98 season and the team got plenty of help from its new members, including Bryan Berard, Sylvain Cote, Curtis Joseph, Alexander Karpovtsev (who led the NHL in plus-minus with +39, but was not eligible for the NHL Plus-Minus Award because he played just 58 games), Yanic Perreault and Steve Thomas (who finished second on the team in points, with 73). Former Vancouver Canucks head coach Pat Quinn replaced Mike Murphy as Toronto's head coach. Six Maple Leafs scored 20 or more goals. Toronto set a club record for most regular season wins (45) and earned 97 points to finish second in the Northeast Division and fourth in the Eastern Conference. They led the NHL in most goals for, with 268, and were the only team to score 200 or more even-strength goals.
On November 12, 1998, the Maple Leafs defeated the Chicago Blackhawks 10–3 away. Mats Sundin recorded a hat trick in the game, which was the first regular season game in which the Leafs had scored ten goals since February 17, 1989, when they defeated the New York Rangers 10–6 away.

### Maple Leaf Gardens

* On February 13, 1999, the Maple Leafs ended a 67-year tradition when they played their last game at Maple Leaf Gardens. The team lost 6–2 to the Chicago Blackhawks. Former Maple Leaf Doug Gilmour scored a fluke goal in that game and notorious tough guy Bob Probert scored the final NHL goal in Gardens history in the game's third period. During the emotional post-game ceremony, legendary Canadian singer Anne Murray performed "The Maple Leaf Forever" while wearing a Toronto jersey. The Leafs were the last of the Original Six teams to leave their Original Six-era arena, three years after the Canadiens did so.

### Air Canada Centre

* The first Maple Leafs home game took place on February 20, 1999, against the Montreal Canadiens, won by the Leafs 3–2 on an overtime goal by Steve Thomas.

### Season standings

Northeast Division :
| R | CR | | GP | W | L | T | GF | GA | PIM | Pts |
| 1 | 2 | Ottawa Senators | 82 | 44 | 23 | 15 | 239 | 179 | 892 | 103 |
| 2 | 4 | Toronto Maple Leafs | 82 | 45 | 30 | 7 | 268 | 231 | 1095 | 97 |
| 3 | 6 | Boston Bruins | 82 | 39 | 30 | 13 | 214 | 181 | 1182 | 91 |
| 4 | 7 | Buffalo Sabres | 82 | 37 | 28 | 17 | 207 | 175 | 1561 | 91 |
| 5 | 11 | Montreal Canadiens | 82 | 32 | 39 | 11 | 184 | 209 | 1299 | 75 |
Note: CR = Conference rank; GP = Games played; W = Wins; L = Losses; T = Ties; GF = Goals for; GA = Goals against; Pts = Points Bolded teams qualified for the playoffs.
Eastern Conference :
| R | | Div | GP | W | L | T | GF | GA | Pts |
| 1 | y – New Jersey Devils | ATL | 82 | 47 | 24 | 11 | 248 | 196 | 105 |
| 2 | y – Ottawa Senators | NE | 82 | 44 | 23 | 15 | 239 | 179 | 103 |
| 3 | y – Carolina Hurricanes | SE | 82 | 34 | 30 | 18 | 210 | 202 | 86 |
| 4 | Toronto Maple Leafs | NE | 82 | 45 | 30 | 7 | 268 | 231 | 97 |
| 5 | Philadelphia Flyers | ATL | 82 | 37 | 26 | 19 | 231 | 196 | 93 |
| 6 | Boston Bruins | NE | 82 | 39 | 30 | 13 | 214 | 181 | 91 |
| 7 | Buffalo Sabres | NE | 82 | 37 | 28 | 17 | 207 | 175 | 91 |
| 8 | Pittsburgh Penguins | ATL | 82 | 38 | 30 | 14 | 242 | 225 | 90 |
| 9 | Florida Panthers | SE | 82 | 30 | 34 | 18 | 210 | 228 | 78 |
| 10 | New York Rangers | ATL | 82 | 33 | 38 | 11 | 217 | 227 | 77 |
| 11 | Montreal Canadiens | NE | 82 | 32 | 39 | 11 | 184 | 209 | 75 |
| 12 | Washington Capitals | SE | 82 | 31 | 45 | 6 | 200 | 218 | 68 |
| 13 | New York Islanders | ATL | 82 | 24 | 48 | 10 | 194 | 244 | 58 |
| 14 | Tampa Bay Lightning | SE | 82 | 19 | 54 | 9 | 179 | 292 | 47 |
Divisions: ATL – Atlantic Division, NE – Northeast Division, SE – Southeast Division
bold – Qualified for playoffs; y – Won division

## Playoffs
### Eastern Conference Finals

The Maple Leafs and Buffalo Sabres met in the Eastern Conference Finals. The Maple Leafs were coming off a six-game series win over the Pittsburgh Penguins, while the Sabres were coming off a six-game series win themselves, over the Boston Bruins. Toronto was having its best playoff since 1994, when they last made a Conference Final series. Buffalo, meanwhile, was in the third round for the second consecutive year. With the series victory, the Sabres advanced to the Stanley Cup Finals for the first time in 24 years.

## Schedule and results
### Regular season

1998–99 regular season :
October: 5–4–1 (home: 1–2–1; road: 4–2–0)
GameResultDateScoreOpponentRecordRecap
1WOctober 10, 19982–1Detroit Red Wings (1998–99)1–0–0Recap
2WOctober 13, 19983–2@ Edmonton Oilers (1998–99)2–0–0Recap
3WOctober 16, 19987–3@ Calgary Flames (1998–99)3–0–0Recap
4LOctober 17, 19981–4@ Vancouver Canucks (1998–99)3–1–0Recap
5TOctober 19, 19982–2 OTNashville Predators (1998–99)3–1–1Recap
6WOctober 23, 19985–3@ Detroit Red Wings (1998–99)4–1–1Recap
7WOctober 24, 19986–4@ Pittsburgh Penguins (1998–99)5–1–1Recap
8LOctober 26, 19980–2Pittsburgh Penguins (1998–99)5–2–1Recap
9LOctober 30, 19981–4@ Buffalo Sabres (1998–99)5–3–1Recap
10LOctober 31, 19983–6Buffalo Sabres (1998–99)5–4–1Recap :
November: 8–5–1 (home: 7–1–1; road: 1–4–0)
GameResultDateScoreOpponentRecordRecap
11WNovember 4, 19983–0Colorado Avalanche (1998–99)6–4–1Recap
12LNovember 5, 19981–4@ Boston Bruins (1998–99)6–5–1Recap
13TNovember 7, 19986–6 OTNew York Rangers (1998–99)6–5–2Recap
14LNovember 9, 19981–3New York Islanders (1998–99)6–6–2Recap
15WNovember 11, 19983–2Edmonton Oilers (1998–99)7–6–2Recap
16WNovember 12, 199810–3@ Chicago Blackhawks (1998–99)8–6–2Recap
17WNovember 14, 19982–1Ottawa Senators (1998–99)9–6–2Recap
18LNovember 18, 19981–4@ Washington Capitals (1998–99)9–7–2Recap
19LNovember 20, 19981–4@ Buffalo Sabres (1998–99)9–8–2Recap
20WNovember 21, 19982–1Buffalo Sabres (1998–99)10–8–2Recap
21WNovember 23, 19983–2Calgary Flames (1998–99)11–8–2Recap
22WNovember 25, 19985–1Vancouver Canucks (1998–99)12–8–2Recap
23LNovember 27, 19983–4@ Philadelphia Flyers (1998–99)12–9–2Recap
24WNovember 28, 19983–2 OTOttawa Senators (1998–99)13–9–2Recap :
December: 8–4–0 (home: 5–3–0; road: 3–1–0)
GameResultDateScoreOpponentRecordRecap
25WDecember 2, 19983–1Los Angeles Kings (1998–99)14–9–2Recap
26WDecember 5, 19984–3 OT@ Montreal Canadiens (1998–99)15–9–2Recap
27LDecember 7, 19982–6@ New York Rangers (1998–99)15–10–2Recap
28WDecember 11, 19983–2@ Chicago Blackhawks (1998–99)16–10–2Recap
29LDecember 12, 19980–3Philadelphia Flyers (1998–99)16–11–2Recap
30WDecember 16, 19985–2Phoenix Coyotes (1998–99)17–11–2Recap
31WDecember 19, 19987–4New York Rangers (1998–99)18–11–2Recap
32WDecember 21, 19987–1Pittsburgh Penguins (1998–99)19–11–2Recap
33LDecember 23, 19981–5Dallas Stars (1998–99)19–12–2Recap
34LDecember 26, 19981–2Montreal Canadiens (1998–99)19–13–2Recap
35WDecember 30, 19984–1Mighty Ducks of Anaheim (1998–99)20–13–2Recap
36WDecember 31, 19984–2@ Detroit Red Wings (1998–99)21–13–2Recap :
January: 7–4–1 (home: 3–1–0; road: 4–3–1)
GameResultDateScoreOpponentRecordRecap
37LJanuary 2, 19992–5Washington Capitals (1998–99)21–14–2Recap
38WJanuary 4, 19995–4 OTTampa Bay Lightning (1998–99)22–14–2Recap
39LJanuary 7, 19991–2@ Boston Bruins (1998–99)22–15–2Recap
40WJanuary 9, 19996–3Boston Bruins (1998–99)23–15–2Recap
41WJanuary 12, 19994–3@ Tampa Bay Lightning (1998–99)24–15–2Recap
42TJanuary 13, 19993–3 OT@ Florida Panthers (1998–99)24–15–3Recap
43WJanuary 16, 19994–3@ Philadelphia Flyers (1998–99)25–15–3Recap
44LJanuary 18, 19992–4@ Carolina Hurricanes (1998–99)25–16–3Recap
45WJanuary 20, 19996–4@ Dallas Stars (1998–99)26–16–3Recap
46WJanuary 21, 19994–2@ St. Louis Blues (1998–99)27–16–3Recap
47LJanuary 28, 19990–6@ Pittsburgh Penguins (1998–99)27–17–3Recap
48WJanuary 30, 19995–3Washington Capitals (1998–99)28–17–3Recap :
February: 6–4–2 (home: 2–2–1; road: 4–2–1)
GameResultDateScoreOpponentRecordRecap
49WFebruary 2, 19993–0@ Tampa Bay Lightning (1998–99)29–17–3Recap
50LFebruary 3, 19992–5@ Florida Panthers (1998–99)29–18–3Recap
51WFebruary 6, 19993–2@ New Jersey Devils (1998–99)30–18–3Recap
52LFebruary 10, 19995–6Carolina Hurricanes (1998–99)30–19–3Recap
53LFebruary 13, 19992–6Chicago Blackhawks (1998–99)30–20–3Recap
54TFebruary 15, 19993–3 OT@ New Jersey Devils (1998–99)30–20–4Recap
55WFebruary 17, 19993–2 OT@ Buffalo Sabres (1998–99)31–20–4Recap
56WFebruary 20, 19993–2 OTMontreal Canadiens (1998–99)32–20–4Recap
57LFebruary 22, 19993–4@ Washington Capitals (1998–99)32–21–4Recap
58TFebruary 24, 19992–2 OTCarolina Hurricanes (1998–99)32–21–5Recap
59WFebruary 25, 19994–1@ New York Islanders (1998–99)33–21–5Recap
60WFebruary 27, 19994–1Florida Panthers (1998–99)34–21–5Recap :
March: 6–7–1 (home: 2–4–1; road: 4–3–0)
GameResultDateScoreOpponentRecordRecap
61LMarch 3, 19992–5New Jersey Devils (1998–99)34–22–5Recap
62WMarch 4, 19994–0@ St. Louis Blues (1998–99)35–22–5Recap
63LMarch 6, 19991–3@ Ottawa Senators (1998–99)35–23–5Recap
64LMarch 8, 19992–3 OT@ New York Rangers (1998–99)35–24–5Recap
65WMarch 9, 19996–1Tampa Bay Lightning (1998–99)36–24–5Recap
66WMarch 11, 19992–1@ New York Islanders (1998–99)37–24–5Recap
67LMarch 13, 19991–2@ Montreal Canadiens (1998–99)37–25–5Recap
68LMarch 17, 19991–4Boston Bruins (1998–99)37–26–5Recap
69WMarch 20, 19993–1New Jersey Devils (1998–99)38–26–5Recap
70LMarch 22, 19991–3Philadelphia Flyers (1998–99)38–27–5Recap
71LMarch 24, 19995–8San Jose Sharks (1998–99)38–28–5Recap
72WMarch 26, 19997–2@ Carolina Hurricanes (1998–99)39–28–5Recap
73TMarch 27, 19992–2 OTBoston Bruins (1998–99)39–28–6Recap
74WMarch 31, 19996–5@ Vancouver Canucks (1998–99)40–28–6Recap :
April: 5–2–1 (home: 3–0–1; road: 2–2–0)
GameResultDateScoreOpponentRecordRecap
75WApril 1, 19995–1@ Edmonton Oilers (1998–99)41–28–6Recap
76WApril 3, 19995–1@ Calgary Flames (1998–99)42–28–6Recap
77TApril 5, 19992–2 OTSt. Louis Blues (1998–99)42–28–7Recap
78WApril 7, 19994–2Ottawa Senators (1998–99)43–28–7Recap
79LApril 8, 19991–3@ Ottawa Senators (1998–99)43–29–7Recap
80WApril 10, 19999–1Florida Panthers (1998–99)44–29–7Recap
81WApril 14, 19993–2 OTNew York Islanders (1998–99)45–29–7Recap
82LApril 17, 19992–3@ Montreal Canadiens (1998–99)45–30–7Recap :
Legend:
  Win (2 points)
  Loss (0 points)
  Tie (1 point) :

### Playoffs

1999 Stanley Cup playoffs :
Eastern Conference Quarterfinals vs. (5) Philadelphia Flyers – Maple Leafs win 4–2
GameResultDateScoreOpponentSeriesRecap
1LApril 22, 19990–3Philadelphia FlyersFlyers lead 1–0Recap
2WApril 24, 19992–1Philadelphia FlyersSeries tied 1–1Recap
3WApril 26, 19992–1@ Philadelphia FlyersMaple Leafs lead 2–1Recap
4LApril 28, 19992–5@ Philadelphia FlyersSeries tied 2–2Recap
5WApril 30, 19992–1 OTPhiladelphia FlyersMaple Leafs lead 3–2Recap
6WMay 2, 19991–0@ Philadelphia FlyersMaple Leafs win 4–2Recap :
Eastern Conference Semifinals vs. (8) Pittsburgh Penguins – Maple Leafs win 4–2
GameResultDateScoreOpponentSeriesRecap
1LMay 7, 19990–2Pittsburgh PenguinsPenguins lead 1–0Recap
2WMay 9, 19994–2Pittsburgh PenguinsSeries tied 1–1Recap
3LMay 11, 19993–4@ Pittsburgh PenguinsPenguins lead 2–1Recap
4WMay 13, 19993–2 OT@ Pittsburgh PenguinsSeries tied 2–2Recap
5WMay 15, 19994–1Pittsburgh PenguinsMaple Leafs lead 3–2Recap
6WMay 17, 19994–3 OT@ Pittsburgh PenguinsMaple Leafs win 4–2Recap :
Eastern Conference Finals vs. (7) Buffalo Sabres – Sabres win 4–1
GameResultDateScoreOpponentSeriesRecap
1LMay 23, 19994–5Buffalo SabresSabres lead 1–0Recap
2WMay 25, 19996–3Buffalo SabresSeries tied 1–1Recap
3LMay 27, 19992–4@ Buffalo SabresSabres lead 2–1Recap
4LMay 29, 19992–5@ Buffalo SabresSabres lead 3–1Recap
5LMay 31, 19992–4Buffalo SabresSabres win 4–1Recap :
Legend:
  Win
  Loss :

## Player statistics
### Scoring

* Position abbreviations: C = Centre; D = Defence; G = Goaltender; LW = Left Wing; RW = Right Wing
* † = Joined team via a transaction (e.g., trade, waivers, signing) during the season. Stats reflect time with the Maple Leafs only.
* ‡ = Left team via a transaction (e.g., trade, waivers, release) during the season. Stats reflect time with the Maple Leafs only.
| No. | Player | Pos | Regular season | Regular season | Regular season | Regular season | Regular season | Regular season | Playoffs | Playoffs | Playoffs | Playoffs | Playoffs | Playoffs |
| No. | Player | Pos | GP | G | A | Pts | +/- | PIM | GP | G | A | Pts | +/- | PIM |
| 13 | Mats Sundin | C | 82 | 31 | 52 | 83 | 22 | 58 | 17 | 8 | 8 | 16 | 2 | 16 |
| 32 | Steve Thomas | LW | 78 | 28 | 45 | 73 | 26 | 33 | 17 | 6 | 3 | 9 | −1 | 12 |
| 94 | Sergei Berezin | RW | 76 | 37 | 22 | 59 | 16 | 12 | 17 | 6 | 6 | 12 | 0 | 4 |
| 7 | Derek King | LW | 81 | 24 | 28 | 52 | 15 | 20 | 16 | 1 | 3 | 4 | 0 | 4 |
| 22 | Igor Korolev | RW | 66 | 13 | 34 | 47 | 11 | 46 | 1 | 0 | 0 | 0 | 0 | 0 |
| 20 | Mike Johnson | RW | 79 | 20 | 24 | 44 | 13 | 35 | 17 | 3 | 2 | 5 | −1 | 4 |
| 11 | Steve Sullivan | C | 63 | 20 | 20 | 40 | 12 | 28 | 13 | 3 | 3 | 6 | −3 | 14 |
| 19 | Fredrik Modin | LW | 67 | 16 | 15 | 31 | 14 | 35 | 8 | 0 | 0 | 0 | −2 | 6 |
| 10 | Garry Valk | LW | 77 | 8 | 21 | 29 | 8 | 53 | 17 | 3 | 4 | 7 | −1 | 22 |
| 3 | Sylvain Cote | D | 79 | 5 | 24 | 29 | 22 | 28 | 17 | 2 | 1 | 3 | −3 | 10 |
| 36 | Dmitri Yushkevich | D | 78 | 6 | 22 | 28 | 25 | 88 | 17 | 1 | 5 | 6 | 7 | 22 |
| 52 | Alexander Karpovtsev† | D | 56 | 2 | 25 | 27 | 38 | 52 | 14 | 1 | 3 | 4 | −7 | 12 |
| 18 | Alyn McCauley | C | 39 | 9 | 15 | 24 | 7 | 2 | — | — | — | — | — | — |
| 28 | Tie Domi | RW | 72 | 8 | 14 | 22 | 5 | 198 | 14 | 0 | 2 | 2 | −1 | 24 |
| 15 | Tomas Kaberle | D | 57 | 4 | 18 | 22 | 3 | 12 | 14 | 0 | 3 | 3 | 0 | 2 |
| 8 | Todd Warriner | LW | 53 | 9 | 10 | 19 | −6 | 28 | 9 | 0 | 0 | 0 | 0 | 2 |
| 34 | Bryan Berard† | D | 38 | 5 | 14 | 19 | 7 | 22 | 17 | 1 | 8 | 9 | −10 | 8 |
| 44 | Yanic Perreault† | C | 12 | 7 | 8 | 15 | 10 | 12 | 17 | 3 | 6 | 9 | −6 | 6 |
| 25 | Jason Smith‡ | D | 60 | 2 | 11 | 13 | −9 | 40 | — | — | — | — | — | — |
| 55 | Danny Markov | D | 57 | 4 | 8 | 12 | 5 | 47 | 17 | 0 | 6 | 6 | 9 | 18 |
| 38 | Yannick Tremblay | D | 35 | 2 | 7 | 9 | 0 | 16 | — | — | — | — | — | — |
| 14 | Darby Hendrickson‡ | C | 35 | 2 | 3 | 5 | −4 | 30 | — | — | — | — | — | — |
| 31 | Curtis Joseph | G | 67 | 0 | 5 | 5 | | 6 | 17 | 0 | 0 | 0 | | 2 |
| 12 | Kris King | LW | 67 | 2 | 2 | 4 | −16 | 105 | 17 | 1 | 1 | 2 | −1 | 25 |
| 39 | Ladislav Kohn | RW | 16 | 1 | 3 | 4 | 1 | 4 | 2 | 0 | 0 | 0 | 0 | 5 |
| 16 | Lonny Bohonos | RW | 7 | 3 | 0 | 3 | 3 | 4 | 9 | 3 | 6 | 9 | 3 | 2 |
| 2 | Dallas Eakins | D | 18 | 0 | 2 | 2 | 3 | 24 | 1 | 0 | 0 | 0 | 0 | 0 |
| 33 | Chris McAllister† | D | 20 | 0 | 2 | 2 | 4 | 39 | 6 | 0 | 1 | 1 | −1 | 4 |
| 42 | Kevyn Adams | C | 1 | 0 | 0 | 0 | 0 | 0 | 7 | 0 | 2 | 2 | −2 | 14 |
| 4 | Kevin Dahl | D | 3 | 0 | 0 | 0 | 0 | 2 | — | — | — | — | — | — |
| 30 | Glenn Healy | G | 9 | 0 | 0 | 0 | | 0 | 1 | 0 | 0 | 0 | | 0 |
| 37 | Jason Podollan‡ | RW | 4 | 0 | 0 | 0 | 0 | 0 | — | — | — | — | — | — |
| 29 | Felix Potvin‡ | G | 5 | 0 | 0 | 0 | | 0 | — | — | — | — | — | — |
| 35 | Jeff Reese† | G | 2 | 0 | 0 | 0 | | 0 | — | — | — | — | — | — |
| 21 | Adam Mair | C | — | — | — | — | — | — | 5 | 1 | 0 | 1 | −1 | 14 |

### Goaltending

* † = Joined team via a transaction (e.g., trade, waivers, signing) during the season. Stats reflect time with the Maple Leafs only.
* ‡ = Left team via a transaction (e.g., trade, waivers, release) during the season. Stats reflect time with the Maple Leafs only.
| No. | Player | Regular season | Regular season | Regular season | Regular season | Regular season | Regular season | Regular season | Regular season | Regular season | Regular season | Playoffs | Playoffs | Playoffs | Playoffs | Playoffs | Playoffs | Playoffs | Playoffs | Playoffs |
| No. | Player | GP | W | L | T | SA | GA | GAA | SV% | SO | TOI | GP | W | L | SA | GA | GAA | SV% | SO | TOI |
| 31 | Curtis Joseph | 67 | 35 | 24 | 7 | 1903 | 171 | 2.56 | .910 | 3 | 4001 | 17 | 9 | 8 | 440 | 41 | 2.43 | .907 | 1 | 1011 |
| 30 | Glenn Healy | 9 | 6 | 3 | 0 | 257 | 27 | 2.97 | .895 | 0 | 546 | 1 | 0 | 0 | 5 | 0 | 0.00 | 1.000 | 0 | 20 |
| 29 | Felix Potvin‡ | 5 | 3 | 2 | 0 | 142 | 19 | 3.81 | .866 | 0 | 299 | — | — | — | — | — | — | — | — | — |
| 35 | Jeff Reese† | 2 | 1 | 1 | 0 | 51 | 8 | 4.53 | .843 | 0 | 106 | — | — | — | — | — | — | — | — | — |

## Awards and records
### Awards

Curtis Joseph was a runner-up for the Lester B. Pearson Award and Vezina Trophy and Pat Quinn was a runner-up for the Jack Adams Award.
| Type | Award/honour | Recipient |
| League (in-season) | NHL All-Star Game selection | Curtis Joseph |
| League (in-season) | NHL All-Star Game selection | Mats Sundin |
| League (in-season) | NHL Player of the Week | Mats Sundin (October 26) |
| League (in-season) | NHL Player of the Week | Sergei Berezin (April 5) |
| Team | Molson Cup | Curtis Joseph |

### Milestones

| Milestone | Player | Date |
| First game | Tomas Kaberle | October 10, 1998 |
| First game | Adam Mair | May 11, 1999 |
| 500th game played | Curtis Joseph | February 10, 1999 |

## Transactions

The Maple Leafs have been involved in the following transactions during the 1998-99 season.

### Trades

| July 2, 1998 | To Calgary FlamesDavid Cooper | To Toronto Maple LeafsLadislav Kohn |
| October 14, 1998 | To New York RangersMathieu Schneider | To Toronto Maple LeafsAlexander Karpovtsev 4th round pick in 1999 (Mirko Murovic) |
| January 9, 1999 | To New York IslandersFelix Potvin 6th round pick in 1999 (Fedor Fedorov) | To Toronto Maple LeafsBryan Berard 6th round pick in 1999 (Jan Socher) |
| February 16, 1999 | To Vancouver CanucksDarby Hendrickson | To Toronto Maple LeafsChris McAllister |
| February 17, 1999 | To Florida PanthersJeff Ware | To Toronto Maple LeafsDavid Nemirovsky |
| March 23, 1999 | To Edmonton OilersJason Smith | To Toronto Maple Leafs4th round pick in 1999 (Jonathan Zion) 2nd round pick in 2000 (Kris Vernarsky) |
| March 23, 1999 | To Los Angeles KingsJason Podollan 3rd round pick in 1999 (Cory Campbell) | To Toronto Maple LeafsYanic Perreault |

### Waivers

| October 5, 1998 | From St. Louis BluesKevin Dahl |

### Expansion Draft

| June 25, 1999 | To Atlanta ThrashersYannick Tremblay |

### Free agents

| Player | Former Team |
| Steve Thomas | New Jersey Devils |
| Dallas Eakins | Florida Panthers |
| Curtis Joseph | Edmonton Oilers |
| Niklas Andersson | San Jose Sharks |
| Garry Valk | Pittsburgh Penguins |
| Glen Featherstone | Chicago Wolves (IHL) |
| Player | New Team |
| Kelly Fairchild | Dallas Stars |
| Mike Craig | San Jose Sharks |
| Marcel Cousineau | New York Islanders |
| Wendel Clark | Tampa Bay Lightning |
| Matt Martin | Dallas Stars |

## Draft picks

Toronto's draft picks at the 1998 NHL Entry Draft held at the Marine Midland Arena in Buffalo, New York.
| Round | # | Player | Nationality | College/Junior/Club team (League) |
| 1 | 10 | Nik Antropov | Kazakhstan | Torpedo Ust-Kamenogorsk (Kazakhstan) |
| 2 | 35 | Petr Svoboda | Czech Republic | BK Havlíčkův Brod (Czech Republic) |
| 3 | 69 | Jamie Hodson | Canada | Brandon Wheat Kings (WHL) |
| 4 | 87 | Alexei Ponikarovsky | Ukraine | Dynamo Moscow-2 (Russia) |
| 5 | 126 | Morgan Warren | Canada | Moncton Wildcats (QMJHL) |
| 6 | 154 | Allan Rourke | Canada | Kitchener Rangers (OHL) |
| 7 | 181 | Jonathan Gagnon | Canada | Cape Breton Screaming Eagles (QMJHL) |
| 8 | 215 | Dwight Wolfe | Canada | Halifax Mooseheads (QMJHL) |
| 8 | 228 | Michal Travnicek | Czech Republic | Chemopetrol Litvínov (Czech Republic) |
| 9 | 236 | Sergei Rostov | Russia | Dynamo Moscow-2 (Russia) |