Oct 10, 2020 | New Jersey Devils Acquire:  Sum: $3,400,000$3,400,000$3,600,000 Change: +$3,400,000+$3,400,000+$3,600,000 |  | Toronto Maple Leafs Acquire:  Sum: $0$0$0 Change: -$3,400,000-$3,400,000-$3,600,000 |
| Oct 7, 2020 | Boston Bruins Acquire:  2021 7th round pick (TOR) Sum: $0$0$0 Change: $0$0$0 | | Toronto Maple Leafs Acquire: Sum: $0$0$0 Change: $0$0$0 |
| Oct 7, 2020 | Florida Panthers Acquire:  Sum: $0$0$0 Change: $0$0$0 | | Toronto Maple Leafs Acquire: Sum: $0$0$0 Change: $0$0$0 |
| Oct 7, 2020 | Ottawa Senators Acquire:  Sum: $0$0$0 Change: $0$0$0 | | Toronto Maple Leafs Acquire: Sum: $0$0$0 Change: $0$0$0 |
| Aug 25, 2020 | Pittsburgh Penguins Acquire:  Sum: $3,200,000$4,675,833$5,892,500 Change: +$1,200,000+$1,197,500+$5,892,500 | | Toronto Maple Leafs Acquire: Sum: $2,000,000$3,478,333$3,192,500 Change: -$1,200,000-$1,197,500+$3,192,500 |
| Feb 24, 2020 | Chicago Blackhawks Acquire:  From VGK: Sum: $850,000$850,000$850,000 Change: -$1,650,000-$1,650,000-$1,650,000 | | Toronto Maple Leafs Acquire: From CHI: Robin Lehner ($2,500,000 retained - 50%) · $2,500,000$2,500,000$2,500,000 From VGK: Sum: $2,500,000$2,500,000$0 Change: +$1,100,000+$1,100,000-$1,100,000 | | Vegas Golden Knights Acquire:  From TOR: Robin Lehner ($1,100,000 retained - 44%) · $1,400,000$1,400,000$1,400,000 Sum: $1,400,000$550,000$0 Change: +$550,000+$550,000+$550,000 |
| Feb 24, 2020 | New York Islanders Acquire:  Sum: $0$700,000$700,000 Change: $0+$25,000+$700,000 | | Toronto Maple Leafs Acquire: Sum: $0$675,000$700,000 Change: $0-$25,000+$700,000 |
| Feb 24, 2020 | Colorado Avalanche Acquire:  Sum: $0$700,000$700,000 Change: $0-$50,000+$700,000 | | Toronto Maple Leafs Acquire: Sum: $0$750,000$750,000 Change: $0+$50,000+$750,000 |
| Feb 22, 2020 | Nashville Predators Acquire:  Sum: $0$725,000$800,000 Change: $0-$25,000+$800,000 | | Toronto Maple Leafs Acquire: Sum: $0$750,000$750,000 Change: $0+$25,000+$750,000 |
| Feb 19, 2020 | Ottawa Senators Acquire: 2021 conditional 6th round pick* (TOR) *Conditions: Sens receive the 2021 6th round pick if Veronneau plays in 10 NHL games for Toronto in 2019-20 or 10 NHL games in 2020-21. Sum: $0$759,166$70,000 Change: $0-$165,834+$70,000 | | Toronto Maple Leafs Acquire: Sum: $0$925,000$70,000 Change: $0+$165,834+$70,000 |
| Feb 19, 2020 | Florida Panthers Acquire: Sum: $0$767,500$70,000 Change: -$750,000+$17,500+$70,000 | | Toronto Maple Leafs Acquire: Sum: $750,000$750,000$750,000 Change: +$750,000-$17,500+$750,000 |
| Feb 5, 2020 | Los Angeles Kings Acquire:  2021 conditional 3rd round pick* (TOR) *Conditions: The 2021 3rd round pick upgrades to a 2nd round pick if either Kyle Clifford re-signs with Toronto OR if the Leafs make the 2019-20 playoffs and Jack Campbell wins 6 regular season games.
Updated conditions: Due the the shortened season, the NHL ruled that the 2021 3rd rounds pick upgrades to a 2021 2nd round pick if the Leafs win their qualifying round series and Jack Campbell gets 2 or more wins OR if Kyle Clifford re-signs with Toronto.
Result: LA Kings will receive the 2021 3rd round pick. Sum: $775,000$775,000$750,000 Change: -$700,000-$700,000+$750,000 | | Toronto Maple Leafs Acquire: Sum: $1,475,000$1,475,000$0 Change: +$700,000+$700,000-$92,400,000 |
| Jul 25, 2019 | St. Louis Blues Acquire:  Sum: $0$700,000$200,000 Change: -$700,000$0+$200,000 | | Toronto Maple Leafs Acquire: Sum: $700,000$700,000$700,000 Change: +$700,000$0+$700,000 |
| Jul 23, 2019 | Toronto Maple Leafs Acquire: Sum: $5,250,000$5,250,000$3,250,000 Change: +$5,250,000+$4,500,000+$3,250,000 | | Vegas Golden Knights Acquire: Sum: $0$750,000$750,000 Change: -$5,250,000-$4,500,000+$750,000 |
| Jul 12, 2019 | St. Louis Blues Acquire: Sum: $0$0$0 Change: $0$0$0 | | Toronto Maple Leafs Acquire: Future Considerations Sum: $0$0$0 Change: $0$0$0 |
| Jul 1, 2019 | Colorado Avalanche Acquire: Sum: $5,250,000$5,250,000$5,250,000 Change: +$2,500,000+$2,500,000+$5,250,000 | | Toronto Maple Leafs Acquire: Tyson Barrie ($2,750,000 retained - 50%) · $2,750,000$2,750,000$0 Sum: $2,750,000$2,750,000$0 Change: -$2,500,000-$2,500,000-$294,000,000 |
| Jul 1, 2019 | Ottawa Senators Acquire: Sum: $6,600,000$6,600,000$6,600,000 Change: +$5,875,000+$5,115,834+$6,600,000 | | Toronto Maple Leafs Acquire: Sum: $725,000$1,484,166$870,000 Change: -$5,875,000-$5,115,834+$870,000 |
| Jun 22, 2019 | 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 22, 2019 | Carolina Hurricanes Acquire:  2020 conditional 1st round pick* (TOR - #13 - Seth Jarvis) *Conditions: If the Leafs pick is top 10 in 2020, the Hurricanes will receive Toronto's 2021 1st round pick instead.
Result: Carolina will receive Leafs 2020 1st round pick. Sum: $6,250,000$6,250,000$4,250,000 Change: +$6,250,000+$6,250,000+$4,250,000 | | Toronto Maple Leafs Acquire: Sum: $0$0$0 Change: -$6,250,000-$6,250,000$0 |
| May 30, 2019 | Minnesota Wild Acquire:  Sum: $0$0$0 Change: $0$0$0 | | Toronto Maple Leafs Acquire: *Conditions: Minnesota must sign Gordeev to an entry-level contract prior to June 1, 2019
Result: Conditions met. Toronto receives the 2020 7th round pick Sum: $0$0$0 Change: $0$0$0 |
| Feb 25, 2019 | Toronto Maple Leafs Acquire: Sum: $874,125$874,125$874,125 Change: -$50,875-$50,875+$874,125 | | Winnipeg Jets Acquire:  Sum: $925,000$925,000$925,000 Change: +$50,875+$50,875+$925,000 |
| Feb 24, 2019 | Nashville Predators Acquire: Future Considerations Sum: $0$0$0 Change: $0-$787,500$0 | | Toronto Maple Leafs Acquire: Sum: $0$787,500$70,000 Change: $0+$787,500+$70,000 |
| Jan 28, 2019 | Los Angeles Kings Acquire: 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 |
