Toronto Maple Leafs trades
| Toronto Maple Leafs acquire | Date | Washington Capitals acquire | ||
|---|---|---|---|---|
 | 2001 3rd round pick (#65-Brendan Bell) | December 11, 2000 | Dmitri Khristich |  |
| Toronto Maple Leafs acquire | Date | Dallas Stars acquire | ||
|---|---|---|---|---|
| future considerations | October 29, 2000 | Gerald Diduck |  |
| Toronto Maple Leafs acquire | Date | Chicago Blackhawks acquire | ||
|---|---|---|---|---|
| Bryan McCabe | October 2, 2000 | Alexander Karpovtsev |  |
| 2001 4th round pick (#115-Vladimir Gusev) | ||||
| Toronto Maple Leafs acquire | Date | Philadelphia Flyers acquire | ||
|---|---|---|---|---|
| rights to Regan Kelly | September 26, 2000 | Chris McAllister |  |
| Toronto Maple Leafs acquire | Date | Anaheim Ducks acquire | ||
|---|---|---|---|---|
| 2000 6th round pick (#179-Vadim Sozinov) | June 25, 2000 | rights to Jonathan Hedstrom |  |
| 2000 7th round pick (#209-Markus Seikola) | ||||
| Toronto Maple Leafs acquire | Date | Los Angeles Kings acquire | ||
|---|---|---|---|---|
| Don MacLean | February 23, 2000 | Craig Charron |  |
| Toronto Maple Leafs acquire | Date | Tampa Bay Lightning acquire | ||
|---|---|---|---|---|
| Darcy Tucker | February 9, 2000 | Mike Johnson |  |
| 2000 4th round pick (#100-Miguel Delisle) | Marek Posmyk | |||
| future considerations (2001 5th round pick (#134-Kyle Wellwood)) | 2000 5th round pick (#161-Pavel Sedov) | |||
| 2000 6th round pick (#191-Aaron Gionet) | ||||
| future considerations (2001 5th round pick (#152-Terry Denike)) | ||||
| Toronto Maple Leafs acquire | Date | Tampa Bay Lightning acquire | ||
|---|---|---|---|---|
| 2000 3rd round pick (#70-Mikael Tellqvist) | November 29, 1999 | Todd Warriner | |
| Toronto Maple Leafs acquire | Date | Boston Bruins acquire | ||
|---|---|---|---|---|
| right to match arbitration award of Dmitri Khristich | October 20, 1999 | 2000 2nd round pick (#59-Ivan Huml) |  |
| Toronto Maple Leafs acquire | Date | St. Louis Blues acquire | ||
|---|---|---|---|---|
| Tyler Harlton | October 20, 1999 | Derek King |  |
| future considerations | ||||
| Toronto Maple Leafs acquire | Date | St. Louis Blues acquire | ||
|---|---|---|---|---|
| Tyler Harlton | October 20, 1999 | Derek King | |
| 2000 8th round pick | 2000 8th round pick | |||
| Toronto Maple Leafs acquire | Date | Chicago Blackhawks acquire | ||
|---|---|---|---|---|
| 2001 2nd round pick (#39-Karel Pilar) | October 8, 1999 | Sylvain Cote | |
| 2001 conditional pick | ||||
| Toronto Maple Leafs acquire | Date | Tampa Bay Lightning acquire | ||
|---|---|---|---|---|
| Cory Cross | October 1, 1999 | Fredrik Modin | |
| 2001 7th round pick (#198-Ivan Kolozvary) | ||||
| Toronto Maple Leafs acquire | Date | New York Islanders acquire | ||
|---|---|---|---|---|
| Craig Charron | August 17, 1999 | Niklas Andersson |  |
| Toronto Maple Leafs acquire | Date | Tampa Bay Lightning acquire | ||
|---|---|---|---|---|
| 2000 9th round pick (#265-Jean-Philippe Cote) | August 5, 1999 | Jeff Reese | |
| 2000 9th round pick (#287-Milan Kopecky) | ||||
| Toronto Maple Leafs acquire | Date | Atlanta Thrashers acquire | ||
|---|---|---|---|---|
| 2001 6th round pick (#168-Maxim Kondratiev) | July 15, 1999 | Martin Prochazka |  |
| Toronto Maple Leafs acquire | Date | Los Angeles Kings acquire | ||
|---|---|---|---|---|
| Yanic Perreault | March 23, 1999 | Jason Podollan | |
| 1999 3rd round pick (#92-Cory Campbell) | ||||
| Toronto Maple Leafs acquire | Date | Edmonton Oilers acquire | ||
|---|---|---|---|---|
| 1999 4th round pick (#110-Jonathan Zion) | March 23, 1999 | Jason Smith |  |
| 2000 2nd round pick (#51-Kris Vernarsky) | ||||
| Toronto Maple Leafs acquire | Date | Florida Panthers acquire | ||
|---|---|---|---|---|
| David Nemirovsky | February 17, 1999 | Jeff Ware |  |
| Toronto Maple Leafs acquire | Date | Vancouver Canucks acquire | ||
|---|---|---|---|---|
| Chris McAllister | February 16, 1999 | Darby Hendrickson |  |