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Transactions
| Date | Player | Pos | Transactions |
| 9/21 | Tanner Gentry | WR | pract. squad add |
| 9/20 | D.J. Tialavea | T | pract. squad add |
| 9/19 | Tanner Gentry | WR | cut |
| 9/19 | Mike Purcell | pract. squad add | |
| 9/19 | DeAndre Houston-Carson | S | active/prac. squad |
| 9/19 | Josh Rounds | RB | pract. squad del |
| 9/12 | Tanner Gentry | WR | active/prac. squad |
| 9/12 | Jonathan Anderson | LB | active/prac. squad |
| 9/12 | Josh Rounds | RB | pract. squad add |
| 9/12 | Mario Alford | WR | pract. squad add |
| 9/12 | Rueben Randle | WR | cut |
| 9/12 | Rueben Randle | WR | off IR hamstring |
| 9/12 | Kevin White | WR | on IR fractured scapula |
| 9/12 | Jerrell Freeman | LB | on IR pectoral, concussion |
| 9/9 | Akiem Hicks | DE | re-signed Four-year extension (through 2021) |
| 9/8 | Ka'Deem Carey | RB | cut |
| 9/8 | Connor Shaw | QB | cut |
| 9/8 | Ka'Deem Carey | RB | off IR wrist |
| 9/8 | Connor Shaw | QB | off IR hamstring |
| 9/6 | Lamarr Houston | LB | cut |
| 9/6 | Lamarr Houston | LB | off IR knee |
| 9/4 | John Jenkins | DT | signed |
| 9/4 | Cameron Lee | G | pract. squad add |
| 9/4 | Chris Prosinski | S | cut |
| 9/4 | Ben Braunecker | TE | pract. squad add |
| 9/4 | Chris Prosinski | S | off IR undisclosed |
| 9/4 | Deiondre' Hall | CB | on IR hamstring |
| 9/3 | Taquan Mizzell | RB | acquired from waiver |
| 9/3 | Andrew DePaola | TE | acquired from waiver |
| 9/3 | Tre McBride | WR | acquired from waiver |
| 9/3 | Ben Braunecker | TE | cut |
| 9/3 | Jeremy Langford | RB | cut |
| 9/3 | Jeff Overbaugh | LB | cut |
| 9/3 | Jonathan Anderson | LB | pract. squad add |
| 9/3 | Rashaad Coward | DT | pract. squad add |
| 9/3 | Tanner Gentry | WR | pract. squad add |
| 9/3 | Brandon Greene | T | pract. squad add |
| 9/3 | DeAndre Houston-Carson | S | pract. squad add |
| 9/3 | Isaiah Irving | LB | pract. squad add |
| 9/3 | Dieugot Joseph | T | pract. squad add |
| 9/3 | John Timu | LB | pract. squad add |
| 9/3 | Connor Shaw | QB | on IR hamstring |
| 9/2 | Roberto Aguayo | K | cut |
| 9/2 | Jonathan Anderson | LB | cut |
| 9/2 | Daniel Braverman | WR | cut |
| 9/2 | Rashaad Coward | DT | cut |
| 9/2 | Titus Davis | WR | cut |
| 9/2 | Tanner Gentry | WR | cut |
| 9/2 | Brandon Greene | T | cut |
| 9/2 | DeAndre Houston-Carson | S | cut |
| 9/2 | Alton Howard | WR | cut |
| 9/2 | Isaiah Irving | LB | cut |
| 9/2 | Harold Jones-Quartey | S | cut |
| 9/2 | Dieugot Joseph | T | cut |
| 9/2 | Mitchell Kirsch | T | cut |
| 9/2 | Will Poehls | T | cut |
| 9/2 | MyCole Pruitt | TE | cut |
| 9/2 | Rashaad Reynolds | CB | cut |
| 9/2 | Cyril Richardson | G | cut |
| 9/2 | Josh Rounds | RB | cut |
| 9/2 | Freddie Stevenson | RB | cut |
| 9/2 | John Timu | LB | cut |
| 9/2 | Johnthan Banks | CB | cut |
| 9/2 | Taylor Boggs | C | cut |
| 9/2 | Victor Cruz | WR | cut |
| 9/2 | Jaye Howard | DT | cut |
| 9/2 | John Jenkins | DT | cut |
| 9/2 | Kelvin Sheppard | LB | cut |
| 9/2 | Dan Skuta | LB | cut |
| 9/2 | B.W. Webb | CB | cut |
| 9/2 | C.J. Wilson | DT | cut |
| 9/2 | Ka'Deem Carey | RB | on IR wrist |
| 9/2 | Lamarr Houston | LB | on IR knee |
| 9/2 | Cameron Meredith | WR | on IR knee |
| 9/2 | Jordan Morgan | G | on IR shoulder |
| 9/2 | Chris Prosinski | S | on IR undisclosed |
| 8/30 | Patrick Scales | TE | on IR torn ACL |
| 8/29 | Kapron Lewis-Moore | DE | cut |
| 8/29 | Alex Scearce | LB | cut |
| 8/28 | Jeff Overbaugh | LB | signed |
| 8/23 | Charles Leno Jr. | T | re-signed Four-year extension (through 2021) |
| 8/18 | Kelvin Sheppard | LB | signed One-year contract (through 2017) |
| 8/18 | Hendrick Ekpe | LB | cut |
| 8/13 | Roberto Aguayo | K | acquired from waiver |
| 8/13 | Rueben Randle | WR | on IR hamstring |
| 8/9 | Joel Bouagnon | RB | cut |
| 8/9 | Joel Bouagnon | RB | off IR undisclosed |
| 8/7 | Andy Phillips | K | cut |
| 8/7 | Alton Howard | WR | signed |
| 8/7 | Brandon Greene | T | signed |
| 8/7 | Eric Kush | G | on IR torn hamstring |
| 8/5 | Joel Bouagnon | RB | on IR undisclosed |
| 8/3 | Josh Rounds | RB | signed |
| 7/19 | Mitchell Trubisky | QB | signed/draft choice Four-year contract (fifth-year option) |
| 5/31 | Franko House | TE | cut |
| 5/31 | Michael Burton | RB | acquired from waiver |
| 5/30 | Jhajuan Seales | WR | cut |
| 5/25 | Victor Cruz | WR | signed One-year contract (through 2017) |
| 5/19 | Adam Shaheen | TE | signed/draft choice Four-year contract (through 2020) |
| 5/15 | Eddie Jackson | S | signed/draft choice Four-year contract (through 2020) |
| 5/14 | Kermit Whitfield | WR | cut |
| 5/14 | Titus Davis | WR | signed |
| 5/11 | Paul Lasike | RB | cut |
| 5/11 | Eddie Royal | WR | cut |
| 5/11 | Cornelius Edison | C | cut |
| 5/11 | Will Sutton | DT | cut |
| 5/11 | Tarik Cohen | RB | signed/draft choice Four-year contract (through 2020) |
| 5/11 | Jordan Morgan | G | signed/draft choice Four-year contract (through 2020) |
| 5/11 | Joel Bouagnon | RB | signed |
| 5/11 | Rashaad Coward | DT | signed |
| 5/11 | Hendrick Ekpe | LB | signed |
| 5/11 | Tanner Gentry | WR | signed |
| 5/11 | Franko House | TE | signed |
| 5/11 | Isaiah Irving | LB | signed |
| 5/11 | Dieugot Joseph | T | signed |
| 5/11 | Mitchell Kirsch | T | signed |
| 5/11 | Andy Phillips | K | signed |
| 5/11 | Kermit Whitfield | WR | signed |
| 5/11 | Freddie Stevenson | RB | signed |
| 5/11 | Jhajuan Seales | WR | signed |
| 5/11 | Alex Scearce | LB | signed |
| 5/8 | Dan Skuta | LB | signed One-year contract (through 2017) |
| 5/5 | Jay Cutler | QB | retired |
| 5/4 | Jaye Howard | DT | signed One-year contract (through 2017) |
| 5/2 | Bradley Sowell | T | signed/unrest FA One-year contract (through 2017) |
| 5/1 | Kyle Fuller | CB | team declines option Fifth-year option on rookie contract |
| 5/1 | Bralon Addison | RB | cut |
| 5/1 | Dres Anderson | WR | cut |
| 5/1 | De'Vante Bausby | CB | cut |
| 5/1 | David Cobb | RB | cut |
| 5/1 | Jacoby Glenn | CB | cut |
| 5/1 | Justin Perillo | TE | cut |
| 5/1 | Taylor Boggs | C | signed |
| 4/17 | Bryce Callahan | CB | re-signed/excl. FA One-year tender (through 2017) |
| 4/15 | Sam Acho | LB | re-signed/unrest FA One-year contract (through 2017) |
| 4/10 | Tracy Porter | CB | cut |
| 4/5 | B.W. Webb | CB | signed/unrest FA One-year contract (through 2017) |
| 3/31 | Ego Ferguson | DT | cut |
| 3/23 | Deonte Thompson | WR | re-signed/unrest FA One-year contract (through 2017) |
| 3/23 | Mark Sanchez | QB | signed/unrest FA One-year contract (through 2017) |
| 3/21 | Benny Cunningham | RB | signed/unrest FA One-year contract (through 2017) |
| 3/20 | Chris Prosinski | S | re-signed/unrest FA One-year contract (through 2017) |
| 3/20 | C.J. Wilson | DT | re-signed/unrest FA One-year contract (through 2017) |
| 3/17 | John Jenkins | DT | signed/unrest FA One-year contract (through 2017) |
| 3/14 | Connor Barth | K | re-signed/unrest FA One-year contract (through 2017) |
| 3/12 | Kendall Wright | WR | signed/unrest FA One-year contract (through 2017) |
| 3/12 | Tom Compton | T | signed/unrest FA One-year contract (through 2017) |
| 3/11 | Christian Jones | LB | re-signed/unrest FA One-year contract (through 2017) |
| 3/11 | Johnthan Banks | CB | re-signed/unrest FA One-year contract (through 2017) |
| 3/11 | Marcus Cooper | CB | signed/unrest FA Three-year contract (through 2019) |
| 3/10 | Markus Wheaton | WR | signed/unrest FA Two-year contract (through 2018) |
| 3/10 | Mike Glennon | QB | signed/unrest FA Three-year contract (through 2019) |
| 3/10 | Dion Sims | TE | signed/unrest FA Three-year contract (through 2019) |
| 3/10 | Prince Amukamara | CB | signed/unrest FA One-year contract (through 2017) |
| 3/9 | Jay Cutler | QB | cut |
| 3/9 | Sam Acho | LB | Declared Free Agent |
| 3/9 | Mike Adams | T | Declared Free Agent |
| 3/9 | Johnthan Banks | CB | Declared Free Agent |
| 3/9 | Matt Barkley | QB | Declared Free Agent |
| 3/9 | David Fales | QB | Declared Free Agent |
| 3/9 | Connor Barth | K | Declared Free Agent |
| 3/9 | Demontre Hurst | CB | Declared Free Agent |
| 3/9 | Nick Becton | T | Declared Free Agent |
| 3/9 | Christian Jones | LB | Declared Free Agent |
| 3/9 | Brandon Boykin | CB | Declared Free Agent |
| 3/9 | Danny Mason | LB | Declared Free Agent |
| 3/9 | Brian Hoyer | QB | Declared Free Agent |
| 3/9 | Alshon Jeffery | WR | Declared Free Agent |
| 3/9 | Ted Larsen | C | Declared Free Agent |
| 3/9 | Matt McCants | T | Declared Free Agent |
| 3/9 | Logan Paulsen | TE | Declared Free Agent |
| 3/9 | Chris Prosinski | S | Declared Free Agent |
| 3/9 | Deonte Thompson | WR | Declared Free Agent |
| 3/9 | Cornelius Washington | DE | Declared Free Agent |
| 3/9 | C.J. Wilson | DT | Declared Free Agent |
| 3/9 | Marquess Wilson | WR | Declared Free Agent |
| 3/9 | Quintin Demps | S | signed/unrest FA Three-year contract (through 2019) |
| 3/6 | Daniel Brown | TE | re-signed One-year contract (through 2017) |
| 3/4 | Connor Shaw | QB | re-signed One-year contract (through 2017) |
| 3/4 | Patrick Scales | TE | re-signed One-year contract (through 2017) |
| 2/15 | Eric Kush | G | re-signed Two-year contract (through 2018) |
Last updated Sep. 21, 5:59 P.M. ET
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