| 02 Oct 99 | r00   | Montreal CanadiensMontreal Cana | 1 - 4 | Toronto Maple LeafsToronto Maple |
| 04 Oct 99 | r00 | Toronto Maple LeafsToronto Maple | 4 - 0 | Boston BruinsBoston Bruins |
| 06 Oct 99 | r00 | Toronto Maple LeafsToronto Maple | 2 - 1 | Colorado AvalancheColorado Aval |
| 09 Oct 99 | r00 | Ottawa SenatorsOttawa Senato | 4 - 3 | Toronto Maple LeafsToronto Maple |
| 11 Oct 99 | r00 | Toronto Maple LeafsToronto Maple | 2 - 4 | Nashville PredatorsNashville Pre |
| 13 Oct 99 | r00 | Toronto Maple LeafsToronto Maple | 3 - 2 | Florida PanthersFlorida Panth |
| 16 Oct 99 | r00 | Chicago BlackhawksChicago Black | 1 - 2 | Toronto Maple LeafsToronto Maple |
| 17 Oct 99 | r00 | St. Louis BluesSt. Louis Blu | 4 - 2 | Toronto Maple LeafsToronto Maple |
| 20 Oct 99 | r00 | Toronto Maple LeafsToronto Maple | 3 - 3 | Carolina HurricanesCarolina Hurr |
| 23 Oct 99 | r00 | Toronto Maple LeafsToronto Maple | 3 - 2 | Montreal CanadiensMontreal Cana |
| 25 Oct 99 | r00 | Toronto Maple LeafsToronto Maple | 4 - 0 | Dallas StarsDallas Stars |
| 27 Oct 99 | r00 | Toronto Maple LeafsToronto Maple | 4 - 0 | Atlanta ThrashersAtlanta Thras |
| 30 Oct 99 | r00 | Toronto Maple LeafsToronto Maple | 2 - 1 | Calgary FlamesCalgary Flame |
| 04 Nov 99 | r00 | Carolina HurricanesCarolina Hurr | 0 - 6 | Toronto Maple LeafsToronto Maple |
| 06 Nov 99 | r00 | Washington CapitalsWashington Ca | 5 - 3 | Toronto Maple LeafsToronto Maple |
| 07 Nov 99 | r00 | New Jersey DevilsNew Jersey De | 3 - 3 | Toronto Maple LeafsToronto Maple |
| 10 Nov 99 | r00 | Toronto Maple LeafsToronto Maple | 0 - 2 | Anaheim DucksAnaheim Ducks |
| 12 Nov 99 | r00 | Boston BruinsBoston Bruins | 4 - 3 | Toronto Maple LeafsToronto Maple |
| 14 Nov 99 | r00 | Toronto Maple LeafsToronto Maple | 1 - 1 | Detroit Red WingsDetroit Red W |
| 16 Nov 99 | r00 | Toronto Maple LeafsToronto Maple | 4 - 2 | San Jose SharksSan Jose Shar |
| 18 Nov 99 | r00 | Toronto Maple LeafsToronto Maple | 2 - 3 | St. Louis BluesSt. Louis Blu |
| 21 Nov 99 | r00 | Toronto Maple LeafsToronto Maple | 4 - 3 | New York RangersNew York Rang |
| 24 Nov 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 3 - 1 | Toronto Maple LeafsToronto Maple |
| 27 Nov 99 | r00 | Philadelphia FlyersPhiladelphia | 3 - 2 | Toronto Maple LeafsToronto Maple |
| 28 Nov 99 | r00 | Toronto Maple LeafsToronto Maple | 5 - 2 | Edmonton OilersEdmonton Oile |
| 30 Nov 99 | r00 | Toronto Maple LeafsToronto Maple | 3 - 1 | Washington CapitalsWashington Ca |
| 03 Dec 99 | r00 | Carolina HurricanesCarolina Hurr | 2 - 2 | Toronto Maple LeafsToronto Maple |
| 05 Dec 99 | r00 | Toronto Maple LeafsToronto Maple | 3 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 07 Dec 99 | r00 | Toronto Maple LeafsToronto Maple | 3 - 2 | Buffalo SabresBuffalo Sabre |
| 10 Dec 99 | r00 | Philadelphia FlyersPhiladelphia | 4 - 2 | Toronto Maple LeafsToronto Maple |
| 12 Dec 99 | r00 | Toronto Maple LeafsToronto Maple | 6 - 4 | Philadelphia FlyersPhiladelphia |
| 14 Dec 99 | r00 | Toronto Maple LeafsToronto Maple | 1 - 3 | Ottawa SenatorsOttawa Senato |
| 16 Dec 99 | r00 | Toronto Maple LeafsToronto Maple | 5 - 1 | New York IslandersNew York Isla |
| 19 Dec 99 | r00 | Toronto Maple LeafsToronto Maple | 2 - 1 | Montreal CanadiensMontreal Cana |
| 21 Dec 99 | r00 | Florida PanthersFlorida Panth | 4 - 6 | Toronto Maple LeafsToronto Maple |
| 22 Dec 99 | r00 | Tampa Bay LightningTampa Bay Lig | 2 - 4 | Toronto Maple LeafsToronto Maple |
| 24 Dec 99 | r00 | Toronto Maple LeafsToronto Maple | 4 - 1 | New Jersey DevilsNew Jersey De |
| 30 Dec 99 | r00 | New York IslandersNew York Isla | 1 - 2 | Toronto Maple LeafsToronto Maple |
| 02 Jan 00 | r00 | Buffalo SabresBuffalo Sabre | 8 - 1 | Toronto Maple LeafsToronto Maple |
| 04 Jan 00 | r00 | Toronto Maple LeafsToronto Maple | 6 - 2 | Buffalo SabresBuffalo Sabre |
| 06 Jan 00 | r00 | New York RangersNew York Rang | 3 - 2 | Toronto Maple LeafsToronto Maple |
| 08 Jan 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 5 - 2 | Toronto Maple LeafsToronto Maple |
| 09 Jan 00 | r00 | Toronto Maple LeafsToronto Maple | 3 - 5 | New York RangersNew York Rang |
| 12 Jan 00 | r00 | Boston BruinsBoston Bruins | 2 - 3 | Toronto Maple LeafsToronto Maple |
| 15 Jan 00 | r00 | Edmonton OilersEdmonton Oile | 2 - 3 | Toronto Maple LeafsToronto Maple |
| 16 Jan 00 | r00 | Calgary FlamesCalgary Flame | 4 - 0 | Toronto Maple LeafsToronto Maple |
| 18 Jan 00 | r00 | Vancouver CanucksVancouver Can | 4 - 5 | Toronto Maple LeafsToronto Maple |
| 23 Jan 00 | r00 | Toronto Maple LeafsToronto Maple | 5 - 5 | Washington CapitalsWashington Ca |
| 25 Jan 00 | r00 | Toronto Maple LeafsToronto Maple | 3 - 3 | Ottawa SenatorsOttawa Senato |
| 27 Jan 00 | r00 | Detroit Red WingsDetroit Red W | 4 - 2 | Toronto Maple LeafsToronto Maple |
| 28 Jan 00 | r00 | New York RangersNew York Rang | 3 - 4 | Toronto Maple LeafsToronto Maple |
| 30 Jan 00 | r00 | Toronto Maple LeafsToronto Maple | 3 - 2 | Los Angeles KingsLos Angeles K |
| 02 Feb 00 | r00 | Tampa Bay LightningTampa Bay Lig | 3 - 5 | Toronto Maple LeafsToronto Maple |
| 04 Feb 00 | r00 | Boston BruinsBoston Bruins | 4 - 2 | Toronto Maple LeafsToronto Maple |
| 10 Feb 00 | r00 | Toronto Maple LeafsToronto Maple | 2 - 4 | Philadelphia FlyersPhiladelphia |
| 13 Feb 00 | r00 | Toronto Maple LeafsToronto Maple | 1 - 4 | Vancouver CanucksVancouver Can |
| 15 Feb 00 | r00 | Toronto Maple LeafsToronto Maple | 2 - 5 | Carolina HurricanesCarolina Hurr |
| 17 Feb 00 | r00 | Toronto Maple LeafsToronto Maple | 3 - 3 | Boston BruinsBoston Bruins |
| 20 Feb 00 | r00 | Montreal CanadiensMontreal Cana | 2 - 1 | Toronto Maple LeafsToronto Maple |
| 24 Feb 00 | r00 | Toronto Maple LeafsToronto Maple | 5 - 3 | Arizona CoyotesArizona Coyot |
| 26 Feb 00 | r00 | New Jersey DevilsNew Jersey De | 1 - 3 | Toronto Maple LeafsToronto Maple |
| 27 Feb 00 | r00 | Toronto Maple LeafsToronto Maple | 5 - 2 | Buffalo SabresBuffalo Sabre |
| 01 Mar 00 | r00 | Atlanta ThrashersAtlanta Thras | 0 - 4 | Toronto Maple LeafsToronto Maple |
| 02 Mar 00 | r00 | Florida PanthersFlorida Panth | 3 - 1 | Toronto Maple LeafsToronto Maple |
| 05 Mar 00 | r00 | Toronto Maple LeafsToronto Maple | 4 - 3 | Montreal CanadiensMontreal Cana |
| 07 Mar 00 | r00 | Vancouver CanucksVancouver Can | 5 - 6 | Toronto Maple LeafsToronto Maple |
| 08 Mar 00 | r00 | Edmonton OilersEdmonton Oile | 0 - 2 | Toronto Maple LeafsToronto Maple |
| 10 Mar 00 | r00 | Calgary FlamesCalgary Flame | 2 - 6 | Toronto Maple LeafsToronto Maple |
| 12 Mar 00 | r00 | Ottawa SenatorsOttawa Senato | 2 - 4 | Toronto Maple LeafsToronto Maple |
| 16 Mar 00 | r00 | Toronto Maple LeafsToronto Maple | 2 - 5 | Chicago BlackhawksChicago Black |
| 17 Mar 00 | r00 | Detroit Red WingsDetroit Red W | 3 - 4 | Toronto Maple LeafsToronto Maple |
| 19 Mar 00 | r00 | Toronto Maple LeafsToronto Maple | 1 - 4 | Atlanta ThrashersAtlanta Thras |
| 23 Mar 00 | r00 | Toronto Maple LeafsToronto Maple | 2 - 5 | New York IslandersNew York Isla |
| 24 Mar 00 | r00 | Ottawa SenatorsOttawa Senato | 3 - 2 | Toronto Maple LeafsToronto Maple |
| 26 Mar 00 | r00 | Toronto Maple LeafsToronto Maple | 5 - 3 | New Jersey DevilsNew Jersey De |
| 30 Mar 00 | r00 | St. Louis BluesSt. Louis Blu | 2 - 3 | Toronto Maple LeafsToronto Maple |
| 31 Mar 00 | r00 | Chicago BlackhawksChicago Black | 4 - 0 | Toronto Maple LeafsToronto Maple |
| 02 Apr 00 | r00 | Washington CapitalsWashington Ca | 3 - 4 | Toronto Maple LeafsToronto Maple |
| 03 Apr 00 | r00 | Buffalo SabresBuffalo Sabre | 3 - 2 | Toronto Maple LeafsToronto Maple |
| 05 Apr 00 | r00 | Toronto Maple LeafsToronto Maple | 2 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 07 Apr 00 | r00 | New York IslandersNew York Isla | 1 - 2 | Toronto Maple LeafsToronto Maple |
| 08 Apr 00 | r00  | Toronto Maple LeafsToronto Maple | 4 - 2 | Tampa Bay LightningTampa Bay Lig |
| |
| 12 Apr 00 | Playoff | Toronto Maple LeafsToronto Maple | 2 - 0 | Ottawa SenatorsOttawa Senato |
| 15 Apr 00 | Playoff | Toronto Maple LeafsToronto Maple | 5 - 1 | Ottawa SenatorsOttawa Senato |
| 17 Apr 00 | Playoff | Ottawa SenatorsOttawa Senato | 4 - 3 | Toronto Maple LeafsToronto Maple |
| 19 Apr 00 | Playoff | Ottawa SenatorsOttawa Senato | 2 - 1 | Toronto Maple LeafsToronto Maple |
| 22 Apr 00 | Playoff | Toronto Maple LeafsToronto Maple | 2 - 1 | Ottawa SenatorsOttawa Senato |
| 24 Apr 00 | Playoff | Ottawa SenatorsOttawa Senato | 2 - 4 | Toronto Maple LeafsToronto Maple |
| |
| 27 Apr 00 | QF | Toronto Maple LeafsToronto Maple | 2 - 1 | New Jersey DevilsNew Jersey De |
| 29 Apr 00 | QF | Toronto Maple LeafsToronto Maple | 0 - 1 | New Jersey DevilsNew Jersey De |
| 01 May 00 | QF | New Jersey DevilsNew Jersey De | 5 - 1 | Toronto Maple LeafsToronto Maple |
| 03 May 00 | QF | New Jersey DevilsNew Jersey De | 2 - 3 | Toronto Maple LeafsToronto Maple |
| 06 May 00 | QF | Toronto Maple LeafsToronto Maple | 3 - 4 | New Jersey DevilsNew Jersey De |
| 08 May 00 | QF | New Jersey DevilsNew Jersey De | 3 - 0 | Toronto Maple LeafsToronto Maple |
Team 1999-2000 Schedules
Anaheim Ducks
Boston Bruins
Buffalo Sabres
Calgary Flames
Carolina Hurricanes
Chicago Blackhawks
Colorado Avalanche
Columbus Blue Jackets
Dallas Stars
Detroit Red Wings
Edmonton Oilers
Florida Panthers
Los Angeles Kings
Minnesota Wild
Montreal Canadiens
Nashville Predators
New Jersey Devils
New York Islanders
New York Rangers
Ottawa Senators
Philadelphia Flyers
Pittsburgh Penguins
San Jose Sharks
Seattle Kraken
St. Louis Blues
Tampa Bay Lightning
Toronto Maple Leafs
Utah Mammoth
Vancouver Canucks
Vegas Golden Knights
Washington Capitals
Winnipeg Jets
List
Download as CSV
= TV Listing
= Banner Image
= Fanart Image
= Timeline Details