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:
2020 4th round pick (VGK) 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:
 2020 3rd round pick (TOR) 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 2020 6th round pick (COL) 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:
2020 3rd round pick (CBJ) 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:
2020 7th round pick (STL) Sum: $0$0$0 Change: $0$0$0 |
| Jun 22, 2019 | Carolina Hurricanes Acquire:
 2020 conditional 1st round pick* (TOR) 2020 7th round pick (TOR) *Conditions: If the Leafs pick is top 10 in 2020, the Hurricanes will receive Toronto's 2021 1st round pick instead. Sum: $6,250,000$6,250,000$4,250,000 Change: +$6,250,000+$6,250,000+$4,250,000 | | Toronto Maple Leafs Acquire:
2020 6th round pick (CAR) 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:
2020 conditional 7th round pick* (WPG) *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 |
| 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:
*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:
 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:
Sum: $0$0$0 Change: -$736,666-$736,666-$800,000 |
