# 1999–2000 Toronto Maple Leafs season

The 1999–2000 Toronto Maple Leafs season saw the team finish in first place for the first time since the 1962–63 season. It was also the Maple Leafs' first 100-point season, the first full season at the Air Canada Centre, as well as long-time NHLer Wendel Clark's last season in the NHL.

## Offseason

* On July 22, 1999, Syl Apps III, the grandson of former Maple Leafs captain Syl Apps, was signed as a free agent by Toronto.

## Regular season

The Maple Leafs had their second consecutive 45-win season and broke the 1992–93 franchise record for most points accumulated in a season. Mats Sundin averaged a point per game, scoring 32 goals and picking up 41 assists for 73 points in 73 games. Jonas Hoglund had a career year, finishing third on the team in points with 56 (29 goals and 27 assists). Goaltender Curtis Joseph set a Maple Leafs record for wins in a season by a goaltender, with 36. The Leafs put Steve Sullivan on waivers and on October 23, 1999, he was picked up by the Chicago Blackhawks. In early 2000, Wendel Clark returned to the Leafs for the third time and had a two-goal game on February 1 in a 5–3 Maple Leafs win at Tampa Bay. In March, the Leafs traded Mike Johnson to Tampa Bay in exchange for Darcy Tucker.
The Leafs got off to a red-hot start to the season, winning 10 of their first 14 games with four shutouts. The team suffered a setback on December 4, 1999, in a home game against the Pittsburgh Penguins. Forward Yanic Perreault was coming around the Pittsburgh net with the puck when Penguins goaltender Tom Barrasso slashed Perreault with his goalie stick. Perreault suffered a broken arm and missed 23 games; Barrasso received a four-game suspension for his actions. Another setback occurred on March 11 at Ottawa, when Senators forward Marian Hossa was attempting to clear the puck out of the centre-ice zone. Hossa swung his stick in a golf-swing motion and caught Toronto defenceman Bryan Berard in his right eye. Berard had to leave the game due to the injury and Hossa was assessed with a double minor for high-sticking. It was the last NHL game Berard would play for nearly a year-and-a-half. Additionally, Sergei Berezin, a 37-goal scorer in 1998–99, missed 21 games for the team, but nonetheless finished with a solid 26 goals for Toronto. Despite these hindrances, the Leafs battled on, defeating four solid teams between March 16 and April 1 (Detroit on March 16, New Jersey on March 25, St. Louis on March 29 and Washington on April 1). The Leafs finished third in the Eastern Conference and first in the Northeast Division—the first time the Leafs had won a division title since 1938. Mats Sundin led all skaters in overtime goals scored, with four.

### All-Star Game

The 50th National Hockey League All-Star Game was part of the 1999–2000 NHL season, and took place in Toronto's Air Canada Centre on February 6, 2000.
The all-star week festivities saw the Canadian Hockey League Top Prospects Game played on February 2, and an exhibition game between the Canadian and American women's national teams on February 3. The Heroes of Hockey game and the Skills Competition were held on February 5. It is to note that the opening face-off for the Heroes of Hockey game were Ted Lindsay and Fleming Mackell, two players who played in the 1st National Hockey League All-Star Game.
The week also was a good sendoff for Wayne Gretzky, who had retired the previous season. His #99 was raised to the rafters, despite him never playing for the hometown Maple Leafs, as a show of his number's League-wide retirement. Gretzky also made it clear that he would not partake in any oldtimer or Heroes of Hockey game unless it was held in Edmonton, a statement that was realized with the 2003 Heritage Classic three years later.

### Season standings

Northeast Division :
| No. | CR | | GP | W | L | T | OTL | GF | GA | Pts |
| 1 | 3 | Toronto Maple Leafs | 82 | 45 | 27 | 7 | 3 | 246 | 222 | 100 |
| 2 | 6 | Ottawa Senators | 82 | 41 | 28 | 11 | 2 | 244 | 210 | 95 |
| 3 | 8 | Buffalo Sabres | 82 | 35 | 32 | 11 | 4 | 213 | 204 | 85 |
| 4 | 10 | Montreal Canadiens | 82 | 35 | 34 | 9 | 4 | 196 | 194 | 83 |
| 5 | 11 | Boston Bruins | 82 | 24 | 33 | 19 | 6 | 210 | 248 | 73 |
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 | OTL | GF | GA | Pts |
| 1 | z – Philadelphia Flyers | AT | 82 | 45 | 22 | 12 | 3 | 237 | 179 | 105 |
| 2 | y – Washington Capitals | SE | 82 | 44 | 24 | 12 | 2 | 227 | 194 | 102 |
| 3 | y – Toronto Maple Leafs | NE | 82 | 45 | 27 | 7 | 3 | 246 | 222 | 100 |
| 4 | New Jersey Devils | AT | 82 | 45 | 24 | 8 | 5 | 251 | 203 | 103 |
| 5 | Florida Panthers | SE | 82 | 43 | 27 | 6 | 6 | 244 | 209 | 98 |
| 6 | Ottawa Senators | NE | 82 | 41 | 28 | 11 | 2 | 244 | 210 | 95 |
| 7 | Pittsburgh Penguins | AT | 82 | 37 | 31 | 8 | 6 | 241 | 236 | 88 |
| 8 | Buffalo Sabres | NE | 82 | 35 | 32 | 11 | 4 | 213 | 204 | 85 |
| 8.5 |||||||||||
| 9 | Carolina Hurricanes | SE | 82 | 37 | 35 | 10 | 0 | 217 | 216 | 84 |
| 10 | Montreal Canadiens | NE | 82 | 35 | 34 | 9 | 4 | 196 | 194 | 83 |
| 11 | New York Rangers | AT | 82 | 29 | 38 | 12 | 3 | 218 | 246 | 73 |
| 12 | Boston Bruins | NE | 82 | 24 | 33 | 19 | 6 | 210 | 248 | 73 |
| 13 | New York Islanders | AT | 82 | 24 | 48 | 9 | 1 | 194 | 275 | 58 |
| 14 | Tampa Bay Lightning | SE | 82 | 19 | 47 | 9 | 7 | 204 | 310 | 54 |
| 15 | Atlanta Thrashers | SE | 82 | 14 | 57 | 7 | 4 | 170 | 313 | 39 |
Divisions: AT – Atlantic, NE – Northeast, SE – Southeast
bold – Qualified for playoffs; z – Won conference; y – Won division

## Schedule and results
### Regular season

1999–2000 regular season :
October: 9–3–1–0 (home: 7–1–1–0; road: 2–2–0–0)
GameResultDateScoreOpponentRecordRecap
1WOctober 2, 19994–1@ Montreal Canadiens (1999–2000)1–0–0–0Recap
2WOctober 4, 19994–0Boston Bruins (1999–2000)2–0–0–0Recap
3WOctober 6, 19992–1Colorado Avalanche (1999–2000)3–0–0–0Recap
4LOctober 9, 19993–4@ Ottawa Senators (1999–2000)3–1–0–0Recap
5LOctober 11, 19992–4Nashville Predators (1999–2000)3–2–0–0Recap
6WOctober 13, 19993–2Florida Panthers (1999–2000)4–2–0–0Recap
7WOctober 15, 19992–1@ Chicago Blackhawks (1999–2000)5–2–0–0Recap
8LOctober 16, 19992–4@ St. Louis Blues (1999–2000)5–3–0–0Recap
9TOctober 20, 19993–3 OTCarolina Hurricanes (1999–2000)5–3–1–0Recap
10WOctober 23, 19993–2Montreal Canadiens (1999–2000)6–3–1–0Recap
11WOctober 25, 19994–0Dallas Stars (1999–2000)7–3–1–0Recap
12WOctober 27, 19994–0Atlanta Thrashers (1999–2000)8–3–1–0Recap
13WOctober 30, 19992–1Calgary Flames (1999–2000)9–3–1–0Recap :
November: 5–4–2–2 (home: 4–2–1–0; road: 1–2–1–2)
GameResultDateScoreOpponentRecordRecap
14WNovember 3, 19996–0@ Carolina Hurricanes (1999–2000)10–3–1–0Recap
15LNovember 5, 19993–5@ Washington Capitals (1999–2000)10–4–1–0Recap
16TNovember 6, 19993–3 OT@ New Jersey Devils (1999–2000)10–4–2–0Recap
17LNovember 9, 19990–2Mighty Ducks of Anaheim (1999–2000)10–5–2–0Recap
18OTLNovember 11, 19993–4 OT@ Boston Bruins (1999–2000)10–5–2–1Recap
19TNovember 13, 19991–1 OTDetroit Red Wings (1999–2000)10–5–3–1Recap
20WNovember 15, 19994–2San Jose Sharks (1999–2000)11–5–3–1Recap
21LNovember 17, 19992–3St. Louis Blues (1999–2000)11–6–3–1Recap
22WNovember 20, 1999 †4–3 OTNew York Rangers (1999–2000)12–6–3–1Recap
23LNovember 23, 19991–3@ Pittsburgh Penguins (1999–2000)12–7–3–1Recap
24OTLNovember 26, 19992–3 OT@ Philadelphia Flyers (1999–2000)12–7–3–2Recap
25WNovember 27, 19995–2Edmonton Oilers (1999–2000)13–7–3–2Recap
26WNovember 29, 19993–1Washington Capitals (1999–2000)14–7–3–2Recap :
December: 9–2–1–0 (home: 6–1–0–0; road: 3–1–1–0)
GameResultDateScoreOpponentRecordRecap
27TDecember 2, 19992–2 OT@ Carolina Hurricanes (1999–2000)14–7–4–2Recap
28WDecember 4, 19993–2 OTPittsburgh Penguins (1999–2000)15–7–4–2Recap
29WDecember 6, 19993–2 OTBuffalo Sabres (1999–2000)16–7–4–2Recap
30LDecember 9, 19992–4@ Philadelphia Flyers (1999–2000)16–8–4–2Recap
31WDecember 11, 19996–4Philadelphia Flyers (1999–2000)17–8–4–2Recap
32LDecember 13, 19991–3Ottawa Senators (1999–2000)17–9–4–2Recap
33WDecember 15, 19995–1New York Islanders (1999–2000)18–9–4–2Recap
34WDecember 18, 19992–1Montreal Canadiens (1999–2000)19–9–4–2Recap
35WDecember 20, 19996–4@ Florida Panthers (1999–2000)20–9–4–2Recap
36WDecember 21, 19994–2@ Tampa Bay Lightning (1999–2000)21–9–4–2Recap
37WDecember 23, 19994–1New Jersey Devils (1999–2000)22–9–4–2Recap
38WDecember 29, 19992–1@ New York Islanders (1999–2000)23–9–4–2Recap :
January: 6–5–2–1 (home: 2–1–2–0; road: 4–4–0–1)
GameResultDateScoreOpponentRecordRecap
39LJanuary 1, 20001–8@ Buffalo Sabres (1999–2000)23–10–4–2Recap
40WJanuary 3, 20006–2Buffalo Sabres (1999–2000)24–10–4–2Recap
41OTLJanuary 5, 20002–3 OT@ New York Rangers (1999–2000)24–10–4–3Recap
42LJanuary 7, 20002–5@ Pittsburgh Penguins (1999–2000)24–11–4–3Recap
43LJanuary 8, 20003–5New York Rangers (1999–2000)24–12–4–3Recap
44WJanuary 11, 20003–2@ Boston Bruins (1999–2000)25–12–4–3Recap
45WJanuary 14, 20003–2 OT@ Edmonton Oilers (1999–2000)26–12–4–3Recap
46LJanuary 15, 20000–4@ Calgary Flames (1999–2000)26–13–4–3Recap
47WJanuary 17, 20005–4 OT@ Vancouver Canucks (1999–2000)27–13–4–3Recap
48TJanuary 22, 20005–5 OTWashington Capitals (1999–2000)27–13–5–3Recap
49TJanuary 24, 20003–3 OTOttawa Senators (1999–2000)27–13–6–3Recap
50LJanuary 26, 20002–4@ Detroit Red Wings (1999–2000)27–14–6–3Recap
51WJanuary 27, 20004–3@ New York Rangers (1999–2000)28–14–6–3Recap
52WJanuary 29, 20003–2Los Angeles Kings (1999–2000)29–14–6–3Recap :
February: 5–5–1–0 (home: 2–3–1–0; road: 3–2–0–0)
GameResultDateScoreOpponentRecordRecap
53WFebruary 1, 20005–3@ Tampa Bay Lightning (1999–2000)30–14–6–3Recap
54LFebruary 3, 20002–4@ Boston Bruins (1999–2000)30–15–6–3Recap
55LFebruary 9, 20002–4Philadelphia Flyers (1999–2000)30–16–6–3Recap
56LFebruary 12, 20001–4Vancouver Canucks (1999–2000)30–17–6–3Recap
57LFebruary 14, 20002–5Carolina Hurricanes (1999–2000)30–18–6–3Recap
58TFebruary 16, 20003–3 OTBoston Bruins (1999–2000)30–18–7–3Recap
59LFebruary 19, 20001–2@ Montreal Canadiens (1999–2000)30–19–7–3Recap
60WFebruary 23, 20005–3Phoenix Coyotes (1999–2000)31–19–7–3Recap
61WFebruary 25, 20003–1@ New Jersey Devils (1999–2000)32–19–7–3Recap
62WFebruary 26, 20005–2Buffalo Sabres (1999–2000)33–19–7–3Recap
63WFebruary 29, 20004–0@ Atlanta Thrashers (1999–2000)34–19–7–3Recap :
March: 8–6–0–0 (home: 2–3–0–0; road: 6–3–0–0)
GameResultDateScoreOpponentRecordRecap
64LMarch 1, 20001–3@ Florida Panthers (1999–2000)34–20–7–3Recap
65WMarch 4, 20004–3Montreal Canadiens (1999–2000)35–20–7–3Recap
66WMarch 6, 20006–5 OT@ Vancouver Canucks (1999–2000)36–20–7–3Recap
67WMarch 7, 20002–0@ Edmonton Oilers (1999–2000)37–20–7–3Recap
68WMarch 9, 20006–2@ Calgary Flames (1999–2000)38–20–7–3Recap
69WMarch 11, 20004–2@ Ottawa Senators (1999–2000)39–20–7–3Recap
70LMarch 15, 20002–5Chicago Blackhawks (1999–2000)39–21–7–3Recap
71WMarch 16, 20004–3 OT@ Detroit Red Wings (1999–2000)40–21–7–3Recap
72LMarch 18, 20001–4Atlanta Thrashers (1999–2000)40–22–7–3Recap
73LMarch 22, 20002–5New York Islanders (1999–2000)40–23–7–3Recap
74LMarch 23, 20002–3@ Ottawa Senators (1999–2000)40–24–7–3Recap
75WMarch 25, 20005–3New Jersey Devils (1999–2000)41–24–7–3Recap
76WMarch 29, 20003–2@ St. Louis Blues (1999–2000)42–24–7–3Recap
77LMarch 30, 20000–4@ Chicago Blackhawks (1999–2000)42–25–7–3Recap :
April: 3–2–0–0 (home: 1–1–0–0; road: 2–1–0–0)
GameResultDateScoreOpponentRecordRecap
78WApril 1, 20004–3@ Washington Capitals (1999–2000)43–25–7–3Recap
79LApril 3, 20002–3@ Buffalo Sabres (1999–2000)43–26–7–3Recap
80LApril 5, 20002–4Pittsburgh Penguins (1999–2000)43–27–7–3Recap
81WApril 7, 20002–1@ New York Islanders (1999–2000)44–27–7–3Recap
82WApril 8, 20004–2Tampa Bay Lightning (1999–2000)45–27–7–3Recap :
Legend:
  Win (2 points)
  Loss (0 points)
  Tie (1 point)
  Overtime loss (1 point) :
* † Hockey Hall of Fame Game

### Playoffs

2000 Stanley Cup playoffs :
Eastern Conference Quarterfinals vs. (6) Ottawa Senators – Maple Leafs win 4–2
GameResultDateScoreOpponentSeriesRecap
1WApril 12, 20002–0Ottawa SenatorsMaple Leafs lead 1–0Recap
2WApril 15, 20005–1Ottawa SenatorsMaple Leafs lead 2–0Recap
3LApril 17, 20003–4@ Ottawa SenatorsMaple Leafs lead 2–1Recap
4LApril 19, 20001–2@ Ottawa SenatorsSeries tied 2–2Recap
5WApril 22, 20002–1Ottawa SenatorsMaple Leafs lead 3–2Recap
6WApril 24, 20004–2@ Ottawa SenatorsMaple Leafs win 4–2Recap :
Eastern Conference Semifinals vs. (4) New Jersey Devils – Devils win 4–2
GameResultDateScoreOpponentSeriesRecap
1WApril 27, 20002–1New Jersey DevilsMaple Leafs lead 1–0Recap
2LApril 29, 20000–1New Jersey DevilsSeries tied 1–1Recap
3LMay 1, 20001–5@ New Jersey DevilsDevils lead 2–1Recap
4WMay 3, 20003–2@ New Jersey DevilsSeries tied 2–2Recap
5LMay 6, 20003–4New Jersey DevilsDevils lead 3–2Recap
6LMay 8, 20000–3@ New Jersey DevilsDevils win 4–2Recap :
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 | 73 | 32 | 41 | 73 | 16 | 46 | 12 | 3 | 5 | 8 | 8 | 10 |
| 32 | Steve Thomas | RW | 81 | 26 | 37 | 63 | 1 | 68 | 12 | 6 | 3 | 9 | 8 | 10 |
| 14 | Jonas Hoglund | LW | 82 | 29 | 27 | 56 | −2 | 10 | 12 | 2 | 4 | 6 | 4 | 2 |
| 22 | Igor Korolev | RW | 80 | 20 | 26 | 46 | 12 | 22 | 12 | 0 | 4 | 4 | −1 | 6 |
| 44 | Yanic Perreault | C | 58 | 18 | 27 | 45 | 3 | 22 | 1 | 0 | 1 | 1 | 0 | 0 |
| 15 | Tomas Kaberle | D | 82 | 7 | 33 | 40 | 3 | 24 | 12 | 1 | 4 | 5 | 2 | 0 |
| 94 | Sergei Berezin | LW | 61 | 26 | 13 | 39 | 8 | 2 | 12 | 4 | 4 | 8 | 2 | 0 |
| 9 | Nik Antropov | C | 66 | 12 | 18 | 30 | 14 | 41 | 3 | 0 | 0 | 0 | 1 | 4 |
| 8 | Dmitri Khristich† | LW | 53 | 12 | 18 | 30 | 8 | 24 | 12 | 1 | 2 | 3 | −3 | 0 |
| 34 | Bryan Berard | D | 64 | 3 | 27 | 30 | 11 | 42 | — | — | — | — | — | — |
| 36 | Dmitri Yushkevich | D | 77 | 3 | 24 | 27 | 2 | 55 | 12 | 1 | 1 | 2 | 4 | 4 |
| 20 | Mike Johnson‡ | RW | 52 | 11 | 14 | 25 | 8 | 23 | — | — | — | — | — | — |
| 10 | Garry Valk | RW | 73 | 10 | 14 | 24 | −2 | 44 | 12 | 1 | 2 | 3 | 2 | 14 |
| 16 | Darcy Tucker† | LW | 27 | 7 | 10 | 17 | 3 | 55 | 12 | 4 | 2 | 6 | 0 | 15 |
| 52 | Alexander Karpovtsev | D | 69 | 3 | 14 | 17 | 9 | 54 | 11 | 0 | 3 | 3 | 4 | 4 |
| 4 | Cory Cross | D | 71 | 4 | 11 | 15 | 13 | 64 | 12 | 0 | 2 | 2 | 1 | 2 |
| 28 | Tie Domi | RW | 70 | 5 | 9 | 14 | −5 | 198 | 12 | 0 | 1 | 1 | −5 | 20 |
| 42 | Kevyn Adams | C | 52 | 5 | 8 | 13 | −7 | 39 | 12 | 1 | 0 | 1 | −2 | 7 |
| 18 | Alyn McCauley | C | 45 | 5 | 5 | 10 | −6 | 10 | 5 | 0 | 0 | 0 | −4 | 6 |
| 55 | Danny Markov | D | 59 | 0 | 10 | 10 | 13 | 28 | 12 | 0 | 3 | 3 | 3 | 10 |
| 12 | Kris King | LW | 39 | 2 | 4 | 6 | 4 | 55 | 1 | 0 | 0 | 0 | 0 | 2 |
| 8 | Todd Warriner‡ | C | 18 | 3 | 1 | 4 | 6 | 2 | — | — | — | — | — | — |
| 17 | Wendel Clark† | LW | 20 | 2 | 2 | 4 | −3 | 21 | 6 | 1 | 1 | 2 | 2 | 4 |
| 2 | Gerald Diduck† | D | 26 | 0 | 3 | 3 | 2 | 33 | 10 | 0 | 1 | 1 | −1 | 14 |
| 33 | Chris McAllister | D | 36 | 0 | 3 | 3 | −4 | 68 | — | — | — | — | — | — |
| 43 | Nathan Dempsey | D | 6 | 0 | 2 | 2 | 2 | 2 | — | — | — | — | — | — |
| 21 | Adam Mair | C | 8 | 1 | 0 | 1 | −1 | 6 | 5 | 0 | 0 | 0 | −3 | 8 |
| 25 | Greg Andrusak | D | 9 | 0 | 1 | 1 | 1 | 4 | 3 | 0 | 0 | 0 | −1 | 2 |
| 3 | Sylvain Cote‡ | D | 3 | 0 | 1 | 1 | 1 | 0 | — | — | — | — | — | — |
| 30 | Glenn Healy | G | 20 | 0 | 1 | 1 | | 2 | — | — | — | — | — | — |
| 31 | Curtis Joseph | G | 63 | 0 | 1 | 1 | | 14 | 12 | 0 | 0 | 0 | | 10 |
| 11 | Steve Sullivan‡ | C | 7 | 0 | 1 | 1 | −1 | 4 | — | — | — | — | — | — |
| 7 | Derek King‡ | LW | 3 | 0 | 0 | 0 | −2 | 2 | — | — | — | — | — | — |
| 24 | D. J. Smith | D | 3 | 0 | 0 | 0 | −1 | 5 | — | — | — | — | — | — |
| 49 | Dmitri Yakushin | D | 2 | 0 | 0 | 0 | 0 | 2 | — | — | — | — | — | — |
| 39 | Jeff Farkas | C | — | — | — | — | — | — | 3 | 1 | 0 | 1 | 2 | 0 |

### Goaltending

| 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 | 63 | 36 | 20 | 7 | 1854 | 158 | 2.49 | .915 | 4 | 3801 | 12 | 6 | 6 | 369 | 25 | 2.06 | .932 | 1 | 729 |
| 30 | Glenn Healy | 20 | 9 | 10 | 0 | 527 | 59 | 3.04 | .888 | 2 | 1164 | — | — | — | — | — | — | — | — | — |

## Awards and records
### Awards

| Type | Award/honour | Recipient |
| League (annual) | King Clancy Memorial Trophy | Curtis Joseph |
| League (in-season) | NHL All-Star Game selection | Curtis Joseph |
| League (in-season) | NHL All-Star Game selection | Pat Quinn (coach) |
| League (in-season) | NHL All-Star Game selection | Mats Sundin |
| League (in-season) | NHL All-Star Game selection | Dmitri Yushkevich |
| League (in-season) | NHL Player of the Week | Curtis Joseph (February 28) |
| League (in-season) | NHL Player of the Week | Yanic Perreault (March 13) |
| Team | Molson Cup | Curtis Joseph |

### Milestones

| Milestone | Player | Date |
| First game | Nik Antropov | October 13, 1999 |
| First game | Dmitri Yakushin | November 29, 1999 |
| First game | Jeff Farkas | May 3, 2000 |
| 25th shutout | Curtis Joseph | November 3, 1999 |
| 1,000th game played | Steve Thomas | February 26, 2000 |

## Transactions

The Maple Leafs have been involved in the following transactions during the 1999–2000 season.

### Trades

| July 15, 1999 | To Atlanta ThrashersMartin Prochazka | To Toronto Maple Leafs6th round pick in 2001 (Maxim Kondratiev) |
| August 5, 1999 | To Tampa Bay LightningJeff Reese 9th round pick in 2000 (Milan Kopecky) | To Toronto Maple Leafs9th round pick in 2000 (Jean-Philippe Cote) |
| August 17, 1999 | To New York IslandersNiklas Andersson | To Toronto Maple LeafsCraig Charron |
| October 1, 1999 | To Tampa Bay LightningFredrik Modin | To Toronto Maple LeafsCory Cross 7th round pick in 2001 (Ivan Kolozvary) |
| October 8, 1999 | To Chicago BlackhawksSylvain Cote | To Toronto Maple Leafs2nd round pick in 2001 (Karel Pilar) |
| October 20, 1999 | To St. Louis BluesDerek King | To Toronto Maple LeafsTyler Harlton |
| October 20, 1999 | To Boston BruinsIvan Huml | To Toronto Maple LeafsDmitri Khristich |
| November 29, 1999 | To Tampa Bay LightningTodd Warriner | To Toronto Maple Leafs3rd round pick in 2000 (Mikael Tellqvist) |
| February 9, 2000 | To Tampa Bay LightningMike Johnson Marek Posmyk 5th round pick in 2000 (Pavel Sedov) 6th round pick in 2000 (Aaron Gionet) 5th round pick in 2001 (Terry Denike) | To Toronto Maple LeafsDarcy Tucker 4th round pick in 2000 (Miguel Delisle) 5th round pick in 2001 (Kyle Wellwood) |
| February 23, 2000 | To Los Angeles KingsCraig Charron | To Toronto Maple LeafsDon MacLean |

### Waivers

| September 27, 1999 | To Atlanta ThrashersLadislav Kohn |
| October 23, 1999 | To Chicago BlackhawksSteve Sullivan |

### Free agents

| Player | Former Team |
| Jonas Hoglund | Montreal Canadiens |
| Greg Andrusak | Pittsburgh Penguins |
| Terran Sandwith | Mighty Ducks of Anaheim |
| Jason Bonsignore | Tampa Bay Lightning |
| Justin Hocking | Chicago Blackhawks |
| Jimmy Waite | Calgary Flames |
| Sebastien Centomo | Undrafted Free Agent |
| Syl Apps III | Undrafted Free Agent |
| Bryan Fogarty | Chicago Blackhawks |
| Wendel Clark | Chicago Blackhawks |
| Gerald Diduck | Phoenix Coyotes |
| Player | New Team |
| Scott Pearson | New York Islanders |
| Kevin Dahl | New York Islanders |
| Dallas Eakins | New York Islanders |

## Draft picks

Toronto's draft picks at the 1999 NHL Entry Draft held at the FleetCenter in Boston, Massachusetts.
| Round | # | Player | Nationality | College/Junior/Club team (League) |
| 1 | 24 | Luca Cereda (C) | Switzerland | HC Ambrì-Piotta (Switzerland) |
| 2 | 60 | Peter Reynolds (D) | Canada | London Knights (OHL) |
| 4 | 108 | Mirko Murovic (LW) | Canada | Moncton Wildcats (QMJHL) |
| 4 | 110 | Jonathan Zion (D) | Canada | Ottawa 67's (OHL) |
| 5 | 151 | Vaclav Zavoral (D) | Czech Republic | Chemopetrol Litvínov Jr. (Czech Republic) |
| 6 | 161 | Jan Sochor (LW) | Czech Republic | Slavia Prague (Czech Republic) |
| 7 | 211 | Vladimir Kulikov (G) | Russia | CSKA Moscow (Russia) |
| 8 | 239 | Pierre Hedin (D) | Sweden | Modo Hockey (Sweden) |
| 9 | 267 | Peter Metcalf (D) | United States | University of Maine (Hockey East) |