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| TEAM | PLAYER | TRANSACTION | RIGHTS ACQUIRED |
|---|---|---|---|
| May 17, 2021 | |||
 Toronto Maple Leafs | Mac Hollowell | Minors  | |
| May 15, 2021 | |||
| Toronto Maple Leafs | Mac Hollowell | NHL from Taxi Squad  | |
| May 11, 2021 | |||
| Toronto Maple Leafs | Mac Hollowell | Taxi Squad | |
| May 6, 2021 | |||
| Toronto Maple Leafs | Mac Hollowell | Minors | |
| May 3, 2021 | |||
| Toronto Maple Leafs | Mac Hollowell | Taxi Squad | |
| Mar 29, 2021 | |||
| Toronto Maple Leafs | Mac Hollowell | Minors | |
| Mar 27, 2021 | |||
| Toronto Maple Leafs | Mac Hollowell | Taxi Squad | |
| Mar 26, 2021 | |||
| Toronto Maple Leafs | Mac Hollowell | Emergency Loan | |
| Mar 23, 2021 | |||
| Toronto Maple Leafs | Mac Hollowell | Taxi Squad | |
| Jan 11, 2021 | |||
| Toronto Maple Leafs | Mac Hollowell | Minors | |
| Jan 3, 2021 | |||
| Toronto Maple Leafs | Mac Hollowell | Recalled from loan | |
| Oct 28, 2020 | |||
| Toronto Maple Leafs | Mac Hollowell | Loan | |
| Sep 25, 2019 | |||
| Toronto Maple Leafs | Mac Hollowell | Minors | |
| Mar 7, 2019 | |||
| Toronto Maple Leafs | Mac Hollowell | Signed to Entry-Level Contract | |
| Jun 23, 2018 | |||
| Toronto Maple Leafs | Mac Hollowell | Drafted | ✔ |