Jul 26, 2021 | Boston Bruins Acquire:  Sum: $0$0$0 Change: $0$0$0 |  | Toronto Maple Leafs Acquire:  Future Considerations Sum: $0$0$0 Change: $0$0$0 |
| Jul 17, 2021 | Pittsburgh Penguins Acquire:  2023 7th round pick (TOR) Sum: $0$764,167$750,000 Change: -$2,940,000-$2,175,833-$2,630,000 | | Toronto Maple Leafs Acquire: Sum: $2,940,000$2,940,000$3,380,000 Change: +$2,940,000+$2,175,833+$2,630,000 |
| Apr 12, 2021 | San Jose Sharks Acquire:  Sum: $925,000$925,000$925,000 Change: +$925,000+$225,000+$225,000 | | Toronto Maple Leafs Acquire: Sum: $0$700,000$700,000 Change: -$925,000-$225,000-$225,000 |
| Apr 12, 2021 | Anaheim Ducks Acquire:  2022 5th round pick (TOR) Sum: $0$0$0 Change: -$950,000-$950,000-$950,000 | | Toronto Maple Leafs Acquire: Sum: $950,000$950,000$950,000 Change: +$950,000+$950,000+$950,000 |
| Apr 11, 2021 | Calgary Flames Acquire:  2022 3rd round pick (TOR) Sum: $0$0$0 Change: -$1,375,000-$1,375,000+$134,750,000 | | Toronto Maple Leafs Acquire: David Rittich ($1,375,000 retained - 50%) · $1,375,000$1,375,000$0 Sum: $1,375,000$1,375,000$0 Change: +$1,375,000+$1,375,000-$134,750,000 |
| Apr 11, 2021 | Columbus Blue Jackets Acquire:  From TOR: 2022 4th round pick (TOR) Sum: $0$0$0 Change: -$2,750,000-$2,750,000+$269,500,000 | | San Jose Sharks Acquire: From CBJ: Nick Foligno ($2,750,000 retained - 50%) · $1,375,000$1,375,000$0 From TOR: Sum: $1,375,000$1,375,000$0 Change: +$1,375,000+$1,375,000-$925,000 | | Toronto Maple Leafs Acquire: From SJS: Nick Foligno ($1,375,000 retained - 50%) · $1,375,000$1,375,000$0 Sum: $1,375,000$1,375,000$0 Change: +$1,375,000+$1,375,000$0 |
| Apr 9, 2021 | Columbus Blue Jackets Acquire: 2022 conditional 7th round pick* (TOR) *Conditions: The pick upgrades to a 6th round pick if Nash appears in 25% of Leafs 2020-21 playoff games
Result: Columbus will receive the 2022 6th round pick. Sum: $0$0$0 Change: -$2,750,000-$2,750,000-$2,750,000 | | Toronto Maple Leafs Acquire: Sum: $2,750,000$2,750,000$2,750,000 Change: +$2,750,000+$2,750,000+$2,750,000 |
| Mar 12, 2021 | Columbus Blue Jackets Acquire: Sum: $0$925,000$70,000 Change: $0$0$0 | | Toronto Maple Leafs Acquire: Sum: $0$925,000$70,000 Change: $0$0$0 |
| Feb 15, 2021 | Carolina Hurricanes Acquire:  Sum: $0$1,625,000$1,325,000 Change: -$1,050,000+$575,000+$275,000 | | Toronto Maple Leafs Acquire: Sum: $1,050,000$1,050,000$1,050,000 Change: +$1,050,000-$575,000-$275,000 |
| 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: 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: *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.
Result: Veronneau did not play in 10 games in either season, the pick does not transfer 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:  *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 |
