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| PLAYER | AGE | POS | TEAM | DATE | TYPE | EXTENSION | STRUCTURE | LENGTH | VALUE | CAP HIT | |
|---|---|---|---|---|---|---|---|---|---|---|---|
 Joey Anderson | 22 | RW |  TOR | Oct. 30, 2020 | Stnd (RFA) | 2-way | 3 | $2,250,000 | $750,000 | ||
| Michael Hutchinson | 30 | G | TOR | Oct. 30, 2020 | Stnd (UFA) | 2-way | 2 | $1,450,000 | $725,000 | ||
| Travis Dermott | 23 | LD/RD | TOR | Oct. 23, 2020 | Stnd (RFA) | 1-way | 1 | $874,125 | $874,125 | ||
| Ilya Mikheyev | 25 | LW, RW | TOR | Oct. 20, 2020 | Stnd (RFA) | 1-way | 2 | $3,290,000 | $1,645,000 | ||
| Joe Thornton | 40 | C, LW | TOR | Oct. 16, 2020 | 35+ (UFA) | 1-way | 1 | $700,000 | $700,000 | ||
| Aaron Dell | 31 | G | TOR | Oct. 13, 2020 | Stnd (UFA) | 1-way | 1 | $800,000 | $800,000 | ||
| Jimmy Vesey | 27 | RW, LW | TOR | Oct. 11, 2020 | Stnd (UFA) | 1-way | 1 | $900,000 | $900,000 | ||
| Travis Boyd | 26 | C, RW | TOR | Oct. 10, 2020 | Stnd (UFA) | 1-way | 1 | $700,000 | $700,000 | ||
| Zach Bogosian | 29 | RD | TOR | Oct. 10, 2020 | Stnd (UFA) | 1-way | 1 | $1,000,000 | $1,000,000 | ||
| Wayne Simmonds | 31 | RW, LW | TOR | Oct. 9, 2020 | Stnd (UFA) | 1-way | 1 | $1,500,000 | $1,500,000 | ||
| TJ Brodie | 30 | LD/RD | TOR | Oct. 9, 2020 | Stnd (UFA) | 1-way | 4 | $20,000,000 | $5,000,000 | ||
| Jason Spezza | 37 | C, RW | TOR | Oct. 5, 2020 | 35+ (UFA) | ✔ | 1-way | 1 | $700,000 | $700,000 | |
| Denis Malgin | 23 | LW, RW | TOR | Oct. 2, 2020 | Stnd (RFA) | ✔ | 1-way | 1 | $700,000 | $700,000 | |
| Teemu Kivihalme | 25 | LD | TOR | Jul. 18, 2020 | Stnd (RFA) | ✔ | 2-way | 2 | $1,450,000 | $725,000 | |
| Adam Brooks | 24 | C | TOR | May 14, 2020 | Stnd (RFA) | ✔ | 2-way | 2 | $1,450,000 | $725,000 | |
| Mikko Lehtonen | 26 | LD | TOR | May 4, 2020 | ELC | 2-way | 1 | $925,000 | $925,000 | ||
| Alexander Barabanov | 26 | RW, LW | TOR | Apr. 7, 2020 | ELC | 2-way | 1 | $925,000 | $925,000 | ||
| Filip Král | 20 | LD | TOR | Apr. 1, 2020 | ELC | 2-way | 3 | $2,430,000 | $810,000 | ||
| Kristians Rubins | 22 | LD | TOR | Apr. 1, 2020 | ELC | 2-way | 2 | $1,570,000 | $785,000 | ||
| Mikhail Abramov | 19 | C | TOR | Mar. 10, 2020 | ELC | 2-way | 3 | $2,505,000 | $809,444 | ||
| Jake Muzzin | 31 | LD | TOR | Feb. 24, 2020 | Stnd (UFA) | ✔ | 1-way | 4 | $22,500,000 | $5,625,000 | |
| Pierre Engvall | 24 | RW, LW | TOR | Feb. 12, 2020 | Stnd (RFA) | ✔ | 1-way | 2 | $2,500,000 | $1,250,000 | |
| Martin Marincin | 28 | LD | TOR | Jan. 10, 2020 | Stnd (UFA) | ✔ | 1-way | 1 | $700,000 | $700,000 | |
| Justin Holl | 28 | RD | TOR | Dec. 31, 2019 | Stnd (UFA) | ✔ | 1-way | 3 | $6,000,000 | $2,000,000 | |
| Nicholas Robertson | 17 | LW, RW | TOR | Sep. 19, 2019 | ELC | 2-way | 3 | $2,560,000 | $796,667 | ||
| Tyler Gaudet | 26 | C | TOR | Jul. 24, 2019 | Stnd (UFA) | 2-way | 1 | $700,000 | $700,000 | ||
| Pontus Åberg | 25 | RW, LW | TOR | Jul. 24, 2019 | Stnd (UFA) | 1-way | 1 | $700,000 | $700,000 | ||
| Kalle Kossila | 26 | C | TOR | Jul. 24, 2019 | Stnd (UFA) | 2-way | 2 | $1,400,000 | $700,000 | ||
| Garrett Wilson | 28 | RW, LW | TOR | Jul. 24, 2019 | Stnd (UFA) | 1-way | 1 | $725,000 | $725,000 | ||
| Alexander Kerfoot | 24 | LW, C, RW | TOR | Jul. 4, 2019 | Stnd (RFA) | 1-way | 4 | $14,000,000 | $3,500,000 | ||
| Cody Ceci | 25 | RD | TOR | Jul. 4, 2019 | Stnd (RFA) | 1-way | 1 | $4,500,000 | $4,500,000 | ||
| Kenny Agostino | 27 | LW | TOR | Jul. 1, 2019 | Stnd (UFA) | 1-way | 2 | $1,475,000 | $737,500 | ||
| Jason Spezza | 36 | C, RW | TOR | Jul. 1, 2019 | 35+ (UFA) | 1-way | 1 | $700,000 | $700,000 | ||
| Kevin Gravel | 27 | LD | TOR | Jul. 1, 2019 | Stnd (UFA) | 1-way | 1 | $700,000 | $700,000 | ||
| Nick Shore | 26 | C | TOR | Jul. 1, 2019 | Stnd (UFA) | 1-way | 1 | $750,000 | $750,000 | ||
| Martin Marincin | 27 | LD | TOR | Jun. 29, 2019 | Stnd (UFA) | ✔ | 1-way | 1 | $700,000 | $700,000 | |
| Andreas Johnsson | 24 | LW, RW | TOR | Jun. 28, 2019 | Stnd (RFA) | ✔ | 1-way | 4 | $13,600,000 | $3,400,000 | |
| Kasperi Kapanen | 22 | RW | TOR | Jun. 28, 2019 | Stnd (RFA) | ✔ | 1-way | 3 | $9,600,000 | $3,200,000 | |
| Michael Hutchinson | 29 | G | TOR | Jun. 27, 2019 | Stnd (UFA) | ✔ | 1-way | 1 | $700,000 | $700,000 | |
| Teemu Kivihalme | 24 | LD | TOR | May 7, 2019 | ELC | 2-way | 1 | $925,000 | $792,500 | ||
| Ilya Mikheyev | 24 | LW, RW | TOR | May 6, 2019 | ELC | 2-way | 1 | $925,000 | $925,000 | ||
| Yegor Korshkov | 22 | RW | TOR | May 1, 2019 | ELC | 2-way | 2 | $1,850,000 | $925,000 | ||
| Joseph Woll | 19 | G | TOR | Mar. 24, 2019 | ELC | 2-way | 3 | $2,400,000 | $800,000 | ||
| Nicolas Petan | 24 | C, LW, RW | TOR | Mar. 21, 2019 | Stnd (RFA) | ✔ | 1-way | 2 | $1,550,000 | $775,000 | |
| Joseph Duszak | 21 | RD | TOR | Mar. 13, 2019 | ELC | 2-way | 2 | $1,600,000 | $800,000 | ||
| Mac Hollowell | 20 | RD | TOR | Mar. 7, 2019 | ELC | 2-way | 3 | $2,399,300 | $799,766 | ||
| Andreas Borgman | 24 | LD | TOR | Mar. 6, 2019 | Stnd (RFA) | ✔ | 2-way | 1 | $700,000 | $700,000 | |
| Garret Sparks | 26 | G | TOR | Mar. 5, 2019 | Stnd (RFA) | ✔ | 1-way | 1 | $750,000 | $750,000 | |
| Trevor Moore | 24 | LW, RW | TOR | Jan. 13, 2019 | Stnd (RFA) | ✔ | 1-way | 2 | $1,550,000 | $775,000 | |
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