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| PLAYER | AGE | POS | TEAM | DATE | TYPE | EXTENSION | STRUCTURE | LENGTH | VALUE | CAP HIT | |
|---|---|---|---|---|---|---|---|---|---|---|---|
 Braeden Kressler | 18 | C |  TOR | Oct 2, 2021 | Entry-Level | 2-way | 3 | $2,505,000 | $835,000 | ||
| William Villeneuve | 19 | RD | TOR | Sep 25, 2021 | Entry-Level | 2-way | 3 | $2,505,000 | $835,000 | ||
| Joseph Duszak | 23 | RD | TOR | Aug 4, 2021 | Standard | 2-way | 1 | $750,000 | $750,000 | ||
| Nick Ritchie | 25 | LW | TOR | Jul 31, 2021 | Standard | 1-way | 2 | $5,000,000 | $2,500,000 | ||
| Brennan Menell | 24 | D | TOR | Jul 31, 2021 | Standard | 2-way | 1 | $750,000 | $750,000 | ||
| Ondrej Kase | 25 | RW | TOR | Jul 30, 2021 | Standard | 1-way | 1 | $1,250,000 | $1,250,000 | ||
| Brett Seney | 25 | C, LW | TOR | Jul 29, 2021 | Standard | 2-way | 1 | $750,000 | $750,000 | ||
| Pavel Gogolev | 21 | RW | TOR | Jul 29, 2021 | Entry-Level | 2-way | 3 | $2,502,500 | $834,167 | ||
| Petr Mrázek | 29 | G | TOR | Jul 28, 2021 | Standard | 1-way | 3 | $11,400,000 | $3,800,000 | ||
| Carl Dahlström | 26 | LD | TOR | Jul 28, 2021 | Standard | 2-way | 1 | $750,000 | $750,000 | ||
| David Kämpf | 26 | C, RW | TOR | Jul 28, 2021 | Standard | 1-way | 2 | $3,000,000 | $1,500,000 | ||
| Michael Bunting | 25 | LW | TOR | Jul 28, 2021 | Standard | 1-way | 2 | $1,900,000 | $950,000 | ||
| Alex Biega | 33 | RD | TOR | Jul 28, 2021 | Standard | 2-way | 1 | $750,000 | $750,000 | ||
| Michael Amadio | 25 | C, RW | TOR | Jul 28, 2021 | Standard | 2-way | 1 | $750,000 | $750,000 | ||
| Kurtis Gabriel | 28 | RW | TOR | Jul 28, 2021 | Standard | 1-way | 1 | $750,000 | $750,000 | ||
| Joseph Woll | 22 | G | TOR | Jul 17, 2021 | Standard | ✔ | 2-way | 1 | $750,000 | $750,000 | |
| Travis Dermott | 24 | LD/RD | TOR | Jul 8, 2021 | Standard | ✔ | 1-way | 2 | $3,000,000 | $1,500,000 | |
| Wayne Simmonds | 32 | RW, LW | TOR | Jun 29, 2021 | Standard | ✔ | 1-way | 2 | $1,800,000 | $900,000 | |
| Jason Spezza | 38 | C, RW | TOR | Jun 16, 2021 | 35+ | ✔ | 1-way | 1 | $750,000 | $750,000 | |
| Pontus Holmberg | 22 | RW, LW | TOR | Jun 4, 2021 | Entry-Level | 2-way | 2 | $1,655,000 | $827,500 | ||
| Erik Källgren | 24 | G | TOR | May 19, 2021 | Standard | 2-way | 2 | $1,500,000 | $750,000 | ||
| Kirill Semyonov | 26 | C | TOR | May 5, 2021 | Entry-Level | 2-way | 1 | $825,000 | $825,000 | ||
| Rodion Amirov | 19 | LW | TOR | Apr 15, 2021 | Entry-Level | 2-way | 3 | $2,775,000 | $925,000 | ||
| Alex Steeves | 21 | C | TOR | Mar 29, 2021 | Entry-Level | 2-way | 3 | $2,502,500 | $834,167 | ||
| Scott Sabourin | 27 | RW | TOR | Feb 7, 2021 | Standard | 2-way | 1 | $700,000 | $700,000 | ||
| Joey Anderson | 22 | RW | TOR | Oct 30, 2020 | Standard | 2-way | 3 | $2,250,000 | $750,000 | ||
| Michael Hutchinson | 30 | G | TOR | Oct 30, 2020 | Standard | 2-way | 2 | $1,450,000 | $725,000 | ||
| Travis Dermott | 23 | LD/RD | TOR | Oct 23, 2020 | Standard | 1-way | 1 | $874,125 | $874,125 | ||
| Ilya Mikheyev | 25 | LW, RW | TOR | Oct 20, 2020 | Standard | 1-way | 2 | $3,290,000 | $1,645,000 | ||
| Joe Thornton | 40 | C, LW | TOR | Oct 16, 2020 | 35+ | 1-way | 1 | $700,000 | $700,000 | ||
| Aaron Dell | 31 | G | TOR | Oct 13, 2020 | Standard | 1-way | 1 | $800,000 | $800,000 | ||
| Jimmy Vesey | 27 | LW, RW | TOR | Oct 11, 2020 | Standard | 1-way | 1 | $900,000 | $900,000 | ||
| Zach Bogosian | 29 | RD | TOR | Oct 10, 2020 | Standard | 1-way | 1 | $1,000,000 | $1,000,000 | ||
| Travis Boyd | 26 | C, RW | TOR | Oct 10, 2020 | Standard | 1-way | 1 | $700,000 | $700,000 | ||
| Wayne Simmonds | 31 | RW, LW | TOR | Oct 9, 2020 | Standard | 1-way | 1 | $1,500,000 | $1,500,000 | ||
| TJ Brodie | 30 | RD | TOR | Oct 9, 2020 | Standard | 1-way | 4 | $20,000,000 | $5,000,000 | ||
| Jason Spezza | 37 | C, RW | TOR | Oct 5, 2020 | 35+ | ✔ | 1-way | 1 | $700,000 | $700,000 | |
| Denis Malgin | 23 | RW, C | TOR | Oct 2, 2020 | Standard | ✔ | 1-way | 1 | $700,000 | $700,000 | |
| Teemu Kivihalme | 25 | LD | TOR | Jul 18, 2020 | Standard | ✔ | 2-way | 2 | $1,450,000 | $725,000 | |
| Adam Brooks | 24 | C | TOR | May 14, 2020 | Standard | ✔ | 2-way | 2 | $1,450,000 | $725,000 | |
| Mikko Lehtonen | 26 | LD | TOR | May 4, 2020 | Entry-Level | 2-way | 1 | $925,000 | $925,000 | ||
| Alexander Barabanov | 26 | RW, LW | TOR | Apr 7, 2020 | Entry-Level | 2-way | 1 | $925,000 | $925,000 | ||
| Kristians Rubins | 22 | LD | TOR | Apr 1, 2020 | Entry-Level | 2-way | 2 | $1,570,000 | $785,000 | ||
| Filip Král | 20 | LD | TOR | Apr 1, 2020 | Entry-Level | 2-way | 3 | $2,430,000 | $810,000 | ||
| Mikhail Abramov | 19 | C | TOR | Mar 10, 2020 | Entry-Level | 2-way | 3 | $2,505,000 | $809,444 | ||
| Jake Muzzin | 31 | LD | TOR | Feb 24, 2020 | Standard | ✔ | 1-way | 4 | $22,500,000 | $5,625,000 | |
| Pierre Engvall | 24 | LW, C | TOR | Feb 12, 2020 | Standard | ✔ | 1-way | 2 | $2,500,000 | $1,250,000 | |
| Martin Marincin | 28 | LD | TOR | Jan 10, 2020 | Standard | ✔ | 1-way | 1 | $700,000 | $700,000 | |
| Justin Holl | 28 | RD | TOR | Dec 31, 2019 | Standard | ✔ | 1-way | 3 | $6,000,000 | $2,000,000 | |
| Nicholas Robertson | 17 | LW | TOR | Sep 19, 2019 | Entry-Level | 2-way | 3 | $2,560,000 | $796,667 | ||
