The 1999–2000 Montreal Canadiens season was the club's 91st season of play. The club failed to qualify for the 2000 Stanley Cup playoffs. Pierre Boivin replaced Ronald Corey as team president of the Canadiens. On September 2, 1999, Molson executive James Arnett announced that Molson would put the franchise up for sale.

Off season
Saku Koivu makes Canadiens history, as the first European to be named the team's captain. He succeeds Vincent Damphousse, who was traded the previous season.

Regular season

Final standings

Schedule and results

|- align="center" bgcolor="#FFBBBB"
|1||L||October 2, 1999||1–4 || align="left"|  Toronto Maple Leafs||0–1–0–0||0 || 
|- align="center" bgcolor="#FFBBBB"
|2||L||October 6, 1999||1–2 || align="left"| @ Edmonton Oilers||0–2–0–0||0 || 
|- align="center" bgcolor="#CCFFCC"
|3||W||October 8, 1999||4–1 || align="left"| @ Calgary Flames||1–2–0–0||2 || 
|- align="center" bgcolor="#FFBBBB"
|4||L||October 9, 1999||1–4 || align="left"| @ Vancouver Canucks||1–3–0–0||2 || 
|- align="center" bgcolor="#FFBBBB"
|5||L||October 12, 1999||1–2 || align="left"|  Florida Panthers||1–4–0–0||2 || 
|- align="center" bgcolor="#CCFFCC"
|6||W||October 14, 1999||5–4 OT|| align="left"| @ Philadelphia Flyers||2–4–0–0||4 || 
|- align="center" bgcolor="#CCFFCC"
|7||W||October 16, 1999||2–1 || align="left"|  Buffalo Sabres||3–4–0–0||6 || 
|- align="center" bgcolor="#FFBBBB"
|8||L||October 18, 1999||2–4 || align="left"|  New York Islanders||3–5–0–0||6 || 
|- align="center" bgcolor="#FFBBBB"
|9||L||October 20, 1999||1–2 || align="left"|  Colorado Avalanche||3–6–0–0||6 || 
|- align="center" bgcolor="#FFBBBB"
|10||L||October 23, 1999||2–3 || align="left"| @ Toronto Maple Leafs||3–7–0–0||6 || 
|- align="center" bgcolor="#FFBBBB"
|11||L||October 27, 1999||0–1 || align="left"|  Chicago Blackhawks||3–8–0–0||6 || 
|- align="center"
|12||T||October 30, 1999||2–2 OT|| align="left"|  New York Rangers||3–8–1–0||7 || 
|-

|- align="center" bgcolor="#FFBBBB"
|13||L||November 3, 1999||2–3 || align="left"| @ New Jersey Devils||3–9–1–0||7 || 
|- align="center" bgcolor="#FF6F6F"
|14||OTL||November 4, 1999||1–2 OT|| align="left"| @ New York Islanders||3–9–1–1||8 || 
|- align="center" bgcolor="#FFBBBB"
|15||L||November 6, 1999||1–2 || align="left"| @ Ottawa Senators||3–10–1–1||8 || 
|- align="center" bgcolor="#FFBBBB"
|16||L||November 10, 1999||4–5 || align="left"| @ Pittsburgh Penguins||3–11–1–1||8 || 
|- align="center" bgcolor="#CCFFCC"
|17||W||November 11, 1999||2–1 || align="left"|  Mighty Ducks of Anaheim||4–11–1–1||10 || 
|- align="center" bgcolor="#CCFFCC"
|18||W||November 13, 1999||4–2 || align="left"|  Atlanta Thrashers||5–11–1–1||12 || 
|- align="center" bgcolor="#FFBBBB"
|19||L||November 16, 1999||1–4 || align="left"|  San Jose Sharks||5–12–1–1||12 || 
|- align="center" bgcolor="#FFBBBB"
|20||L||November 18, 1999||1–6 || align="left"| @ Nashville Predators||5–13–1–1||12 || 
|- align="center" bgcolor="#CCFFCC"
|21||W||November 20, 1999||5–3 || align="left"| @ Los Angeles Kings||6–13–1–1||14 || 
|- align="center" bgcolor="#CCFFCC"
|22||W||November 22, 1999||2–1 || align="left"| @ Mighty Ducks of Anaheim||7–13–1–1||16 || 
|- align="center" bgcolor="#CCFFCC"
|23||W||November 23, 1999||3–2 OT|| align="left"| @ San Jose Sharks||8–13–1–1||18 || 
|- align="center" bgcolor="#CCFFCC"
|24||W||November 27, 1999||2–1 || align="left"|  Vancouver Canucks||9–13–1–1||20 || 
|-

|- align="center" bgcolor="#FFBBBB"
|25||L||December 1, 1999||2–3 || align="left"|  Dallas Stars||9–14–1–1||20 || 
|- align="center" bgcolor="#FFBBBB"
|26||L||December 3, 1999||2–3 || align="left"| @ New York Rangers||9–15–1–1||20 || 
|- align="center" bgcolor="#FFBBBB"
|27||L||December 4, 1999||2–3 || align="left"|  Philadelphia Flyers||9–16–1–1||20 || 
|- align="center"
|28||T||December 7, 1999||3–3 OT|| align="left"|  Calgary Flames||9–16–2–1||21 || 
|- align="center" bgcolor="#CCFFCC"
|29||W||December 9, 1999||4–2 || align="left"| @ New York Islanders||10–16–2–1||23 || 
|- align="center" bgcolor="#FFBBBB"
|30||L||December 11, 1999||2–4 || align="left"|  Los Angeles Kings||10–17–2–1||23 || 
|- align="center" bgcolor="#CCFFCC"
|31||W||December 13, 1999||1–0 || align="left"| @ Washington Capitals||11–17–2–1||25 || 
|- align="center" bgcolor="#FFBBBB"
|32||L||December 16, 1999||1–2 || align="left"|  New Jersey Devils||11–18–2–1||25 || 
|- align="center" bgcolor="#FFBBBB"
|33||L||December 18, 1999||1–2 || align="left"| @ Toronto Maple Leafs||11–19–2–1||25 || 
|- align="center" bgcolor="#CCFFCC"
|34||W||December 20, 1999||5–1 || align="left"|  Pittsburgh Penguins||12–19–2–1||27 || 
|- align="center"
|35||T||December 23, 1999||3–3 OT|| align="left"| @ Boston Bruins||12–19–3–1||28 || 
|- align="center"
|36||T||December 27, 1999||4–4 OT|| align="left"| @ Ottawa Senators||12–19–4–1||29 || 
|- align="center" bgcolor="#FFBBBB"
|37||L||December 29, 1999||2–3 || align="left"|  Ottawa Senators||12–20–4–1||29 || 
|-

|- align="center"
|38||T||January 2, 2000||2–2 OT|| align="left"|  New York Rangers||12–20–5–1||30 || 
|- align="center" bgcolor="#FFBBBB"
|39||L||January 4, 2000||1–6 || align="left"| @ Washington Capitals||12–21–5–1||30 || 
|- align="center" bgcolor="#FFBBBB"
|40||L||January 6, 2000||3–4 || align="left"| @ St. Louis Blues||12–22–5–1||30 || 
|- align="center" bgcolor="#FFBBBB"
|41||L||January 7, 2000||1–4 || align="left"| @ Colorado Avalanche||12–23–5–1||30 || 
|- align="center" bgcolor="#CCFFCC"
|42||W||January 11, 2000||3–0 || align="left"|  Detroit Red Wings||13–23–5–1||32 || 
|- align="center" bgcolor="#CCFFCC"
|43||W||January 14, 2000||2–1 || align="left"| @ Buffalo Sabres||14–23–5–1||34 || 
|- align="center"
|44||T||January 15, 2000||2–2 OT|| align="left"|  Boston Bruins||14–23–6–1||35 || 
|- align="center" bgcolor="#CCFFCC"
|45||W||January 19, 2000||3–0 || align="left"|  New York Islanders||15–23–6–1||37 || 
|- align="center" bgcolor="#CCFFCC"
|46||W||January 22, 2000||4–2 || align="left"|  Pittsburgh Penguins||16–23–6–1||39 || 
|- align="center" bgcolor="#FF6F6F"
|47||OTL||January 24, 2000||2–3 OT|| align="left"| @ Carolina Hurricanes||16–23–6–2||40 || 
|- align="center"
|48||T||January 29, 2000||2–2 OT|| align="left"|  Philadelphia Flyers||16–23–7–2||41 || 
|- align="center" bgcolor="#CCFFCC"
|49||W||January 30, 2000||3–0 || align="left"|  Carolina Hurricanes||17–23–7–2||43 || 
|-

|- align="center" bgcolor="#FFBBBB"
|50||L||February 2, 2000||1–3 || align="left"| @ Florida Panthers||17–24–7–2||43 || 
|- align="center" bgcolor="#CCFFCC"
|51||W||February 3, 2000||2–1 OT|| align="left"| @ Tampa Bay Lightning||18–24–7–2||45 || 
|- align="center" bgcolor="#FF6F6F"
|52||OTL||February 8, 2000||4–5 OT|| align="left"|  Edmonton Oilers||18–24–7–3||46 || 
|- align="center" bgcolor="#FFBBBB"
|53||L||February 10, 2000||0–1 || align="left"|  Washington Capitals||18–25–7–3||46 || 
|- align="center" bgcolor="#CCFFCC"
|54||W||February 12, 2000||5–4 || align="left"|  Ottawa Senators||19–25–7–3||48 || 
|- align="center" bgcolor="#CCFFCC"
|55||W||February 14, 2000||4–1 || align="left"|  Florida Panthers||20–25–7–3||50 || 
|- align="center" bgcolor="#CCFFCC"
|56||W||February 16, 2000||5–1 || align="left"| @ Atlanta Thrashers||21–25–7–3||52 || 
|- align="center" bgcolor="#CCFFCC"
|57||W||February 17, 2000||3–0 || align="left"| @ Carolina Hurricanes||22–25–7–3||54 || 
|- align="center" bgcolor="#CCFFCC"
|58||W||February 19, 2000||2–1 || align="left"|  Toronto Maple Leafs||23–25–7–3||56 || 
|- align="center" bgcolor="#CCFFCC"
|59||W||February 22, 2000||1–0 || align="left"|  Phoenix Coyotes||24–25–7–3||58 || 
|- align="center" bgcolor="#CCFFCC"
|60||W||February 24, 2000||3–2 OT|| align="left"|  New Jersey Devils||25–25–7–3||60 || 
|- align="center" bgcolor="#FFBBBB"
|61||L||February 26, 2000||0–3 || align="left"|  Washington Capitals||25–26–7–3||60 || 
|- align="center" bgcolor="#FFBBBB"
|62||L||February 27, 2000||0–3 || align="left"| @ New Jersey Devils||25–27–7–3||60 || 
|-

|- align="center" bgcolor="#CCFFCC"
|63||W||March 1, 2000||4–1 || align="left"| @ Chicago Blackhawks||26–27–7–3||62 || 
|- align="center" bgcolor="#CCFFCC"
|64||W||March 2, 2000||5–2 || align="left"| @ Boston Bruins||27–27–7–3||64 || 
|- align="center" bgcolor="#FFBBBB"
|65||L||March 4, 2000||3–4 || align="left"| @ Toronto Maple Leafs||27–28–7–3||64 || 
|- align="center" bgcolor="#CCFFCC"
|66||W||March 6, 2000||3–2 || align="left"|  Atlanta Thrashers||28–28–7–3||66 || 
|- align="center" bgcolor="#CCFFCC"
|67||W||March 8, 2000||3–0 || align="left"| @ Pittsburgh Penguins||29–28–7–3||68 || 
|- align="center" bgcolor="#CCFFCC"
|68||W||March 10, 2000||3–2 || align="left"| @ Buffalo Sabres||30–28–7–3||70 || 
|- align="center" bgcolor="#FFBBBB"
|69||L||March 11, 2000||3–5 || align="left"|  Boston Bruins||30–29–7–3||70 || 
|- align="center" bgcolor="#FFBBBB"
|70||L||March 14, 2000||3–4 || align="left"|  Tampa Bay Lightning||30–30–7–3||70 || 
|- align="center"
|71||T||March 16, 2000||1–1 OT|| align="left"| @ Philadelphia Flyers||30–30–8–3||71 || 
|- align="center" bgcolor="#CCFFCC"
|72||W||March 18, 2000||3–2 || align="left"|  Carolina Hurricanes||31–30–8–3||73 || 
|- align="center" bgcolor="#FFBBBB"
|73||L||March 20, 2000||1–4 || align="left"| @ Buffalo Sabres||31–31–8–3||73 || 
|- align="center"
|74||T||March 22, 2000||1–1 OT|| align="left"| @ Atlanta Thrashers||31–31–9–3||74 || 
|- align="center" bgcolor="#FFBBBB"
|75||L||March 25, 2000||2–4 || align="left"| @ Florida Panthers||31–32–9–3||74 || 
|- align="center" bgcolor="#CCFFCC"
|76||W||March 26, 2000||3–1 || align="left"| @ Tampa Bay Lightning||32–32–9–3||76 || 
|- align="center" bgcolor="#CCFFCC"
|77||W||March 29, 2000||4–3 || align="left"|  Boston Bruins||33–32–9–3||78 || 
|-

|- align="center" bgcolor="#FFBBBB"
|78||L||April 1, 2000||0–2 || align="left"|  Buffalo Sabres||33–33–9–3||78 || 
|- align="center" bgcolor="#FF6F6F"
|79||OTL||April 2, 2000||5–6 OT|| align="left"| @ Detroit Red Wings||33–33–9–4||79 || 
|- align="center" bgcolor="#CCFFCC"
|80||W||April 5, 2000||3–0 || align="left"| @ New York Rangers||34–33–9–4||81 || 
|- align="center" bgcolor="#CCFFCC"
|81||W||April 6, 2000||5–1 || align="left"|  Tampa Bay Lightning||35–33–9–4||83 || 
|- align="center" bgcolor="#FFBBBB"
|82||L||April 8, 2000||1–3 || align="left"|  Ottawa Senators||35–34–9–4||83 || 
|-

|-
| Legend:

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 Canadiens only.
  = Left team via a transaction (e.g., trade, waivers, release) during the season. Stats reflect time with the Canadiens only.

Goaltending

Awards and records

Awards
Head coach Alain Vigneault was a runner-up for the Jack Adams Trophy.

Transactions

Draft picks
Montreal's draft picks at the 1999 NHL Entry Draft held at the FleetCenter in Boston, Massachusetts.

See also
 1999–2000 NHL season

References

Montreal Canadiens seasons
Montreal Canadiens season, 1999-2000
Montreal