Jan 28, 2019 | Los Angeles Kings Acquire:
 2019 1st round pick (TOR) Sum: $0$925,000$70,000 Change: -$4,000,000-$3,075,000+$70,000 |  | Toronto Maple Leafs Acquire:
 Sum: $4,000,000$4,000,000$4,450,000 Change: +$4,000,000+$3,075,000+$4,450,000 |
| Jan 11, 2019 | Ottawa Senators Acquire:
 Sum: $0$700,000$80,000 Change: $0-$42,500+$80,000 | | Toronto Maple Leafs Acquire:
Sum: $0$742,500$70,000 Change: $0+$42,500+$70,000 |
| Dec 29, 2018 | Florida Panthers Acquire:
 2020 5th round pick (TOR) Sum: $0$0$0 Change: -$275,000-$1,300,000$0 | | Toronto Maple Leafs Acquire:
Sum: $275,000$1,300,000$1,300,000 Change: +$275,000+$1,300,000+$1,300,000 |
| Dec 10, 2018 | Anaheim Ducks Acquire:
 Sum: $0$650,000$650,000 Change: $0$0+$650,000 | | Toronto Maple Leafs Acquire:
Sum: $0$650,000$650,000 Change: $0$0+$650,000 |
| Dec 3, 2018 | Toronto Maple Leafs Acquire:
Sum: $0$675,000$60,000 Change: -$925,000-$250,000-$865,000 | | Vancouver Canucks Acquire:
 Sum: $925,000$925,000$925,000 Change: +$925,000+$250,000+$865,000 |
| Nov 27, 2018 | Calgary Flames Acquire:
 Sum: $0$697,500$70,000 Change: -$700,000-$2,500-$630,000 | | Toronto Maple Leafs Acquire:
Sum: $700,000$700,000$700,000 Change: +$700,000+$2,500+$630,000 |
| Oct 1, 2018 | Dallas Stars Acquire:
 Sum: $1,300,000$1,300,000$1,300,000 Change: +$1,300,000+$1,300,000+$1,300,000 | | Toronto Maple Leafs Acquire:
2019 conditional 7th round pick* (DAL) *Conditions: If Carrick plays in at least 50 games the 2018-19 season, Leafs will receive a 6th round pick in 2019 instead.
Result: The condition was not met. Leafs receive the 2019 7th round pick. Sum: $0$0$0 Change: -$1,300,000-$1,300,000$0 |
| Jul 3, 2018 | New York Islanders Acquire:
 Sum: $2,500,000$2,500,000$2,250,000 Change: +$1,575,000+$1,575,000+$1,325,000 | | Toronto Maple Leafs Acquire:
Sum: $925,000$925,000$925,000 Change: -$1,575,000-$1,575,000-$1,325,000 |
| Jun 23, 2018 | Buffalo Sabres Acquire:
 2019 6th round pick (TOR) Sum: $0$0$0 Change: $0$0$0 | | Toronto Maple Leafs Acquire:
Sum: $0$0$0 Change: $0$0$0 |
| Jun 22, 2018 | St. Louis Blues Acquire:
 Sum: $0$0$0 Change: $0$0$0 | | Toronto Maple Leafs Acquire:
Sum: $0$0$0 Change: $0$0$0 |
| Jun 8, 2018 | Edmonton Oilers Acquire:
 Sum: $0$817,500$792,500 Change: $0+$817,500+$792,500 | | Toronto Maple Leafs Acquire:
2020 conditional 7th round pick* (EDM) *Conditions: Unknown Sum: $0$0$0 Change: $0-$817,500$0 |
| Feb 25, 2018 | Montreal Canadiens Acquire:
 Sum: $0$1,641,666$1,582,500 Change: -$3,000,000-$1,983,334-$1,567,500 | | Toronto Maple Leafs Acquire:
Tomas Plekanec ($3,000,000 retained - 50%) · $3,000,000$3,000,000$2,500,000 Sum: $3,000,000$3,625,000$3,150,000 Change: +$3,000,000+$1,983,334+$1,567,500 |
| Feb 20, 2018 | San Jose Sharks Acquire:
 Eric Fehr · $975,000$2,000,000$2,000,000 (AHL/JR) Sum: $975,000$2,000,000$2,000,000 Change: +$975,000+$2,000,000+$2,000,000 | | Toronto Maple Leafs Acquire:
2020 7th round pick (SJS) Sum: $0$0$0 Change: -$975,000-$2,000,000-$2,000,000 |
| Feb 16, 2018 | St. Louis Blues Acquire:
Sum: $736,666$736,666$800,000 Change: +$736,666+$736,666+$800,000 | | Toronto Maple Leafs Acquire:
2019 4th round pick (STL) Sum: $0$0$0 Change: -$736,666-$736,666-$800,000 |
| Oct 6, 2017 | Toronto Maple Leafs Acquire:
Sum: $0$1,000,000$1,075,000 Change: $0+$306,667+$1,005,000 | | Vegas Golden Knights Acquire:
 Sum: $0$693,333$70,000 Change: -$1,000,000-$306,667-$1,005,000 |
| Mar 1, 2017 | Pittsburgh Penguins Acquire:
 Sum: $0$600,000$600,000 Change: -$2,575,000-$1,975,000-$1,700,000 | | Toronto Maple Leafs Acquire:
Sum: $2,000,000$2,575,000$2,300,000 Change: +$2,000,000+$1,975,000+$1,700,000 |
| Feb 27, 2017 | Tampa Bay Lightning Acquire:
 *Conditions: Based on final draft position, Tampa Bay will acquire the highest pick of the 3 picks Toronto owns in the 2017 draft (Ottawa 2nd round pick, San Jose 2nd round pick and Toronto 2nd round pick)
Result: Tampa Bay will acquire Maple Leafs 2nd round pick Sum: $0$575,000$100,000 Change: -$2,000,000-$1,425,000-$1,900,000 | | Toronto Maple Leafs Acquire:
Sum: $2,000,000$2,000,000$2,000,000 Change: +$2,000,000+$1,425,000+$1,900,000 |
| Feb 18, 2017 | New Jersey Devils Acquire:
 Sum: $0$692,500$70,000 Change: -$800,000-$107,500-$730,000 | | Toronto Maple Leafs Acquire:
Sum: $0$800,000$800,000 Change: $0+$107,500+$730,000 |
| Jan 11, 2017 | Anaheim Ducks Acquire:
Sum: $750,000$750,000$750,000 Change: +$750,000+$750,000+$750,000 | | Toronto Maple Leafs Acquire:
Sum: $0$0$0 Change: -$750,000-$750,000$0 |
| Dec 9, 2016 | Arizona Coyotes Acquire:
 Sum: $1,300,000$1,300,000$1,300,000 Change: +$1,300,000+$1,300,000+$1,300,000 | | Toronto Maple Leafs Acquire:
*Conditions: Leafs receive 2018 6th round pick if Arizona re-signs or trades Peter Holland. If not traded or re-signed, Leafs do not acquire the pick.
Result: Conditions not met. Arizona retains the 2018 6th round pick. Sum: $0$0$0 Change: -$1,300,000-$1,300,000-$1,300,000 |
| Jul 8, 2016 | Anaheim Ducks Acquire:
Sum: $4,150,000$4,150,000$4,150,000 Change: +$4,150,000+$4,150,000+$4,150,000 | | Toronto Maple Leafs Acquire:
2017 conditional draft pick*
*Conditions- — If Bernier starts half of Anaheim’s playoff games next spring and the Ducks win the Stanley Cup, Toronto receives the Ducks’ 2017 second-round pick. (If Anaheim doesn’t still own that selection, it will transfer its next available second-rounder from a future year.)
— If Bernier starts half of Anaheim’s playoff games next spring and the Ducks lose in the Stanley Cup Final, Toronto receives the Ducks’ 2017 third-round pick. (If Anaheim doesn’t still own that selection, it will transfer its next available third-rounder from a future year.)
— Should Anaheim trade Bernier to a team that starts him in half of its playoff games next spring and wins the Stanley Cup, Toronto receives the Ducks’ second-round pick.
— Should Anaheim trade Bernier to a team that starts him in half of its playoff games next spring and loses in the Stanley Cup Final, Toronto receives the Ducks’ third-round pick.
Result: Condition not met. Sum: $0$0$0 Change: -$4,150,000-$4,150,000-$4,150,000 |
| Jun 25, 2016 | Columbus Blue Jackets Acquire:
 *Conditions: If Scott Harrington gets claimed through waivers in the 2016/17 season, Columbus acquires Toronto's 2017 5th round pick. If Harrington does not get claimed on waivers, Leafs retain the 2017 5th round pick.
Result: Harrington did not get claimed through waivers in the 2016/17 season. Leafs retain the 2017 5th round pick. Sum: $632,500$632,500$632,500 Change: +$632,500-$230,833+$562,500 | | Toronto Maple Leafs Acquire:
Sum: $0$863,333$70,000 Change: -$632,500+$230,833-$562,500 |
| Jun 20, 2016 | Anaheim Ducks Acquire:
*Conditions: Based on final draft position, Anaheim will acquire the middle pick of the 3 picks Toronto owns in the 2017 draft (Ottawa 2nd round pick, San Jose 2nd round pick and Toronto 2nd round pick)
Result: Anaheim will receive Sharks 2nd round pick. Sum: $0$0$0 Change: -$5,000,000-$5,000,000$0 | | Toronto Maple Leafs Acquire:
Sum: $5,000,000$5,000,000$5,000,000 Change: +$5,000,000+$5,000,000+$5,000,000 |
| Feb 28, 2016 | Toronto Maple Leafs Acquire:
Sum: $4,500,000$5,136,667$4,070,000 Change: +$2,250,000+$2,886,667+$1,370,000 | | Washington Capitals Acquire:
 Sum: $2,250,000$2,250,000$2,700,000 Change: -$2,250,000-$2,886,667-$1,370,000 |
