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| PLAYER | AGE | POS | TEAM | DATE | TYPE | LENGTH | VALUE | CAP HIT | |
 Kody Clark | 19 | RW |  | Oct 22, 2018 | Entry-Level | 3 | $2,775,000 | $870,000 | |
| Alex Tuch | 22 | RW |  | Oct 19, 2018 | Standard | 7 | $33,250,000 | $4,750,000 | |
| Nick Ritchie | 22 | LW |  | Oct 18, 2018 | Standard | 3 | $4,600,000 | $1,640,000 | |
| Matej Pekar | 18 | C, RW |  | Oct 17, 2018 | Entry-Level | 3 | $2,775,000 | $775,833 | |
| Cory Conacher | 28 | LW |  | Oct 17, 2018 | Standard | 1 | $700,000 | $700,000 | |
| Jake Dotchin | 24 | D | | Oct 17, 2018 | Standard | 1 | $800,000 | $800,000 | |
| Mackenzie Entwistle | 19 | C |  | Oct 16, 2018 | Entry-Level | 3 | $2,775,000 | $842,500 | |
| Stephen Gionta | 35 | C, RW |  | Oct 13, 2018 | Standard | 1 | $650,000 | $650,000 | |
| Drew Stafford | 32 | RW, LW |  | Oct 5, 2018 | Standard | 1 | $810,000 | $810,000 | |
| Cale Fleury | 19 | D |  | Oct 4, 2018 | Entry-Level | 3 | $2,650,000 | $771,666 | |
| Barclay Goodrow | 25 | RW, C |  | Oct 4, 2018 | Standard | 2 | $1,850,000 | $925,000 | |
| Alex Chiasson | 28 | RW |  | Oct 2, 2018 | Standard | 1 | $650,000 | $650,000 | |
| Jason Garrison | 33 | D | | Oct 2, 2018 | Standard | 1 | $650,000 | $650,000 | |
| Riley Sutter | 18 | RW | | Sep 29, 2018 | Entry-Level | 3 | $2,775,000 | $817,500 | |
| Jared McIsaac | 18 | D |  | Sep 28, 2018 | Entry-Level | 3 | $2,775,000 | $792,500 | |
| Jakub Lauko | 18 | C, LW |  | Sep 28, 2018 | Entry-Level | 3 | $2,775,000 | $817,500 | |
| Michael Prapavessis | 22 | D |  | Sep 27, 2018 | Entry-Level | 2 | $1,450,000 | $725,000 | |
| Mark Letestu | 33 | C, RW | | Sep 27, 2018 | Standard | 1 | $750,000 | $750,000 | |
| Michal Cajkovsky | 26 | D |  | Sep 27, 2018 | Standard | 1 | $650,000 | $650,000 | |
| Brandon Davidson | 27 | D | | Sep 27, 2018 | Standard | 1 | $650,000 | $650,000 | |
| Ryan Haggerty | 25 | RW |  | Sep 25, 2018 | Standard | 2 | $1,350,000 | $675,000 | |
| Shea Theodore | 23 | D | | Sep 25, 2018 | Standard | 7 | $36,400,000 | $5,200,000 | |
| Jérémy Groleau | 18 | D | | Sep 24, 2018 | Entry-Level | 3 | $2,170,000 | $723,333 | |
| Alexander Alexeyev | 18 | D | | Sep 24, 2018 | Entry-Level | 3 | $2,775,000 | $925,000 | |
| Luca Sbisa | 28 | D | | Sep 24, 2018 | Standard | 1 | $1,500,000 | $1,500,000 | |
| Paul Byron | 29 | LW, RW | | Sep 23, 2018 | Standard | 4 | $13,600,000 | $3,400,000 | |
| Jacob McGrew | 19 | C | | Sep 22, 2018 | Entry-Level | 3 | $2,550,000 | $768,333 | |
| Miles Wood | 23 | LW | | Sep 22, 2018 | Standard | 4 | $11,000,000 | $2,750,000 | |
| Semyon Der-Arguchintsev | 18 | C |  | Sep 21, 2018 | Entry-Level | 3 | $2,400,000 | $800,000 | |
| Joël Teasdale | 19 | C | | Sep 21, 2018 | Entry-Level | 3 | $2,330,000 | $753,333 | |
| Josh Brook | 19 | D | | Sep 21, 2018 | Entry-Level | 3 | $2,775,000 | $809,166 | |
| Yegor Zamula | 18 | D |  | Sep 20, 2018 | Entry-Level | 3 | $2,350,000 | $753,333 | |
| Sam Reinhart | 22 | RW, C | | Sep 19, 2018 | Standard | 2 | $7,300,000 | $3,650,000 | |
| Ty Dellandrea | 18 | C |  | Sep 19, 2018 | Entry-Level | 3 | $4,387,500 | $925,000 | |
| Darnell Nurse | 23 | D | | Sep 17, 2018 | Standard | 2 | $6,400,000 | $3,200,000 | |
| Joshua Morrissey | 23 | D |  | Sep 16, 2018 | Standard | 2 | $6,300,000 | $3,150,000 | |
| Tyler Seguin | 26 | C, RW | | Sep 13, 2018 | Standard | 8 | $78,800,000 | $9,850,000 | |
| Benjamin Gleason | 20 | D | | Sep 13, 2018 | Entry-Level | 3 | $2,285,000 | $761,666 | |
| Jordan Schmaltz | 24 | D |  | Sep 12, 2018 | Standard | 2 | $1,400,000 | $700,000 | |
| Max Pacioretty | 29 | LW | | Sep 10, 2018 | Standard | 4 | $28,000,000 | $7,000,000 | |
| Michael McCarron | 23 | RW, C | | Sep 10, 2018 | Standard | 1 | $874,125 | $874,125 | |
| Matt Puempel | 25 | LW | | Sep 9, 2018 | Standard | 2 | $1,350,000 | $675,000 | |
| Eric Comrie | 23 | G | | Sep 6, 2018 | Standard | 1 | $650,000 | $650,000 | |
| Blake Wheeler | 32 | RW | | Sep 4, 2018 | Standard | 5 | $41,250,000 | $8,250,000 | |
| Sergei Shumakov | 25 | RW | | Sep 1, 2018 | Entry-Level | 1 | $1,350,000 | $925,000 | |
| Noah Hanifin | 21 | D |  | Aug 30, 2018 | Standard | 6 | $29,700,000 | $4,950,000 | |
| JC Lipon | 25 | RW | | Aug 29, 2018 | Standard | 1 | $650,000 | $650,000 | |
| Troy Brouwer | 33 | RW |  | Aug 27, 2018 | Standard | 1 | $850,000 | $850,000 | |
| Kristian Vesalainen | 19 | LW, RW | | Aug 26, 2018 | Entry-Level | 3 | $4,475,000 | $925,000 | |
| Drake Rymsha | 20 | C |  | Aug 25, 2018 | Entry-Level | 3 | $2,200,000 | $733,333 | |
