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| PLAYER | AGE | POS | TEAM | DATE | TYPE | EXTENSION | STRUCTURE | LENGTH | VALUE | CAP HIT | |
|---|---|---|---|---|---|---|---|---|---|---|---|
 Cade Webber | 22 | LD |  TOR | Apr. 18, 2024 | ELC | 2-way | 2 | $1,750,000 | $875,000 | ||
| Nicolas Mattinen | 26 | D | TOR | Apr. 14, 2024 | Stnd (UFA) | 2-way | 1 | $775,000 | $775,000 | ||
| Jacob Quillan | 22 | C | TOR | Apr. 1, 2024 | ELC | 2-way | 2 | $1,750,000 | $875,000 | ||
| Simon Benoit | 25 | LD | TOR | Mar. 29, 2024 | Stnd (RFA) | ✔ | 1-way | 3 | $4,050,000 | $1,350,000 | |
| Bobby McMann | 28 | RW, LW | TOR | Mar. 13, 2024 | Stnd (UFA) | ✔ | 1-way | 2 | $2,700,000 | $1,350,000 | |
| William Nylander | 28 | RW | TOR | Jan. 8, 2024 | Stnd (UFA) | ✔ | 1-way | 8 | $92,000,000 | $11,500,000 | |
| Noah Chadwick | 18 | LD | TOR | Dec. 22, 2023 | ELC | 2-way | 3 | $2,555,000 | $851,667 | ||
| Noah Gregor | 24 | LW, RW | TOR | Oct. 10, 2023 | Stnd (UFA) | 1-way | 1 | $775,000 | $775,000 | ||
| Simon Benoit | 24 | LD | TOR | Aug. 28, 2023 | Stnd (UFA) | 1-way | 1 | $775,000 | $775,000 | ||
| Auston Matthews | 26 | C | TOR | Aug. 23, 2023 | Stnd (UFA) | ✔ | 1-way | 4 | $53,000,000 | $13,250,000 | |
| Easton Cowan | 18 | LW, C | TOR | Aug. 10, 2023 | ELC | 2-way | 3 | $2,807,500 | $935,833 | ||
| Martin Jones | 33 | G | TOR | Aug. 9, 2023 | Stnd (UFA) | 1-way | 1 | $875,000 | $875,000 | ||
| Nick Abruzzese | 24 | LW, C | TOR | Jul. 31, 2023 | Stnd (RFA) | 2-way | 2 | $1,550,000 | $775,000 | ||
| Ilya Samsonov | 26 | G | TOR | Jul. 23, 2023 | Stnd (RFA) | 1-way | 1 | $3,550,000 | $3,550,000 | ||
| Dylan Gambrell | 26 | C | TOR | Jul. 3, 2023 | Stnd (UFA) | 1-way | 1 | $775,000 | $775,000 | ||
| Max Domi | 28 | C, RW | TOR | Jul. 2, 2023 | Stnd (UFA) | 1-way | 1 | $3,000,000 | $3,000,000 | ||
| Tyler Bertuzzi | 28 | LW, RW | TOR | Jul. 2, 2023 | Stnd (UFA) | 1-way | 1 | $5,500,000 | $5,500,000 | ||
| Marshall Rifai | 25 | LD | TOR | Jul. 1, 2023 | Stnd (UFA) | 2-way | 2 | $1,550,000 | $775,000 | ||
| Maxime Lajoie | 25 | LD | TOR | Jul. 1, 2023 | Stnd (UFA) | 2-way | 1 | $775,000 | $775,000 | ||
| John Klingberg | 30 | RD | TOR | Jul. 1, 2023 | Stnd (UFA) | 1-way | 1 | $4,150,000 | $4,150,000 | ||
| William Lagesson | 27 | LD/RD | TOR | Jul. 1, 2023 | Stnd (UFA) | 2-way | 1 | $775,000 | $775,000 | ||
| Ryan Reaves | 36 | RW | TOR | Jul. 1, 2023 | 35+ (UFA) | 1-way | 3 | $4,050,000 | $1,350,000 | ||
| Artur Akhtiamov | 21 | G | TOR | Jul. 1, 2023 | ELC | 2-way | 3 | $2,555,000 | $851,667 | ||
| David Kämpf | 28 | C | TOR | Jun. 28, 2023 | Stnd (UFA) | ✔ | 1-way | 4 | $9,600,000 | $2,400,000 | |
| Pontus Holmberg | 24 | C, LW | TOR | Jun. 28, 2023 | Stnd (RFA) | ✔ | 1-way | 2 | $1,600,000 | $800,000 | |
| Vyacheslav Peksa | 20 | G | TOR | May 15, 2023 | ELC | 2-way | 3 | $2,555,000 | $851,667 | ||
| Matthew Knies | 19 | LW, RW | TOR | Apr. 9, 2023 | ELC | 2-way | 3 | $2,775,000 | $925,000 | ||
| Ryan Tverberg | 21 | RW, C | TOR | Mar. 15, 2023 | ELC | 2-way | 3 | $2,555,000 | $851,667 | ||
| Conor Timmins | 24 | RD | TOR | Feb. 9, 2023 | Stnd (RFA) | ✔ | 1-way | 2 | $2,200,000 | $1,100,000 | |
| Keith Petruzzelli | 23 | G | TOR | Nov. 6, 2022 | ELC | 2-way | 2 | $1,635,000 | $817,500 | ||
| Fraser Minten | 17 | C, LW | TOR | Oct. 13, 2022 | ELC | 2-way | 3 | $2,625,000 | $845,833 | ||
| Zach Aston-Reese | 27 | LW, RW | TOR | Oct. 9, 2022 | Stnd (UFA) | 1-way | 1 | $840,630 | $840,630 | ||
| Rasmus Sandin | 22 | LD | TOR | Sep. 29, 2022 | Stnd (RFA) | 1-way | 2 | $2,800,000 | $1,400,000 | ||
| Pierre Engvall | 26 | RW, LW | TOR | Jul. 17, 2022 | Stnd (RFA) | 1-way | 1 | $2,250,000 | $2,250,000 | ||
| Calle Järnkrok | 30 | RW, C, LW | TOR | Jul. 15, 2022 | Stnd (UFA) | 1-way | 4 | $8,400,000 | $2,100,000 | ||
| Victor Mete | 24 | LD/RD | TOR | Jul. 14, 2022 | Stnd (UFA) | 1-way | 1 | $750,000 | $750,000 | ||
| Jordie Benn | 34 | LD/RD | TOR | Jul. 14, 2022 | Stnd (UFA) | 1-way | 1 | $750,000 | $750,000 | ||
| Denis Malgin | 25 | LW, RW | TOR | Jul. 13, 2022 | Stnd (RFA) | 1-way | 1 | $750,000 | $750,000 | ||
| Nicolas Aubé-Kubel | 26 | RW | TOR | Jul. 13, 2022 | Stnd (UFA) | 1-way | 1 | $1,000,000 | $1,000,000 | ||
| Dennis Hildeby | 20 | G | TOR | Jul. 13, 2022 | ELC | 2-way | 3 | $2,530,000 | $843,333 | ||
| Ilya Samsonov | 25 | G | TOR | Jul. 13, 2022 | Stnd (UFA) | 1-way | 1 | $1,800,000 | $1,800,000 | ||
| Adam Gaudette | 25 | C, RW | TOR | Jul. 13, 2022 | Stnd (UFA) | 1-way | 1 | $750,000 | $750,000 | ||
| Timothy Liljegren | 23 | RD | TOR | Jun. 27, 2022 | Stnd (RFA) | ✔ | 1-way | 2 | $2,800,000 | $1,400,000 | |
| Mark Giordano | 38 | LD | TOR | May 22, 2022 | 35+ (UFA) | ✔ | 1-way | 2 | $1,600,000 | $800,000 | |
| Topi Niemelä | 20 | RD | TOR | May 13, 2022 | ELC | 2-way | 3 | $2,570,000 | $856,667 | ||
| Roni Hirvonen | 20 | LW | TOR | May 13, 2022 | ELC | 2-way | 3 | $2,570,000 | $856,667 | ||
| Bobby McMann | 26 | RW, LW | TOR | Apr. 29, 2022 | Stnd (UFA) | 2-way | 2 | $1,525,000 | $762,500 | ||
| Axel Rindell | 22 | RD | TOR | Apr. 8, 2022 | ELC | 2-way | 2 | $1,677,500 | $838,750 | ||
| Max Ellis | 22 | RW | TOR | Apr. 8, 2022 | ELC | 2-way | 2 | $1,677,500 | $838,750 | ||
| Mikko Kokkonen | 21 | LD | TOR | Mar. 30, 2022 | ELC | 2-way | 3 | $2,540,000 | $846,667 | ||
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