| Last updated: Wed, November 19, 2008, 19:42 EST |
| Date | Player | Pos. | Transaction |
| 11/17 | Kelvin Jimenez | P | Acquired Off Waivers From, Toronto |
| 11/14 | Mike MacDougal | P | Outrighted to Minors |
| 11/13 | Wilson Betemit | 1B | Traded From, NY Yankees (for OF Nick Swisher in five-player deal) |
| 11/4 | Ken Griffey Jr. | RF | Declared Free Agency, (team option declined) |
| 11/1 | Orlando Cabrera | SS | Declared Free Agency |
| 10/31 | Horacio Ramirez | P | Declared Free Agency |
| 10/31 | Toby Hall | C | Declared Free Agency, (team option declined) |
| 10/30 | Juan Uribe | 2B | Declared Free Agency |
| 10/30 | Ken Griffey Jr. | RF | Not Offered Contract and Became Free Agent, (team option declined) |
| 10/30 | Joe Crede | 3B | Declared Free Agency |
| 10/28 | Jayson Nix | 2B | Signed as Free Agent, ( 2009) |
| 9/21 | Jim Thome | DH | Signed, ( 2009)(option vested) |
| 9/6 | Charlie Haeger | P | Designated for Assignment |
| 9/5 | Dewayne Wise | CF | Removed From 15-Day DL, (Strained left adductor) |
| 9/2 | Lance Broadway | P | Called Up from Minors |
| 9/2 | Chris Getz | 2B | Called Up from Minors |
| 9/2 | Josh Fields | 3B | Called Up from Minors |
| 9/1 | Paul Phillips | C | Purchased From Minors |
| 9/1 | Jose Contreras | P | Transferred to 60-Day DL, (Ruptured left Achilles tendon) |
| 9/1 | Scott Linebrink | P | Removed From 15-Day DL, (Right shoulder inflammation) |
| 9/1 | Mike MacDougal | P | Called Up from Minors |
| 9/1 | Jerry Owens | CF | Called Up from Minors |
| 9/1 | Ehren Wassermann | P | Called Up from Minors |
| 8/31 | Lance Broadway | P | Sent to Minors |
| 8/25 | Dewayne Wise | CF | Placed on 15-Day DL, (Strained left adductor) |
| 8/25 | Chris Getz | 2B | Sent to Minors |
| 8/25 | Joe Crede | 3B | Removed From 15-Day DL, (Back lumbar inflammation) |
| 8/25 | Joe Crede | 3B | Recalled From Minors, Rehab Assignment |
| 8/25 | Lance Broadway | P | Called Up from Minors |
| 8/19 | Joe Crede | 3B | Sent to Minors, For Rehabilitation |
| 8/15 | Clayton Richard | P | Called Up from Minors |
| 8/14 | Lance Broadway | P | Sent to Minors |
| 8/11 | Franklyn German | P | Traded From, Pittsburgh (for player to be named) |
| 8/10 | Jose Contreras | P | Placed on 15-Day DL, (Ruptured left Achilles tendon) |
| 8/10 | Lance Broadway | P | Called Up from Minors |
| 8/10 | Boone Logan | P | Sent to Minors |
| 8/9 | Jose Contreras | P | Recalled From Minors, Rehab Assignment |
| 8/9 | Ehren Wassermann | P | Sent to Minors |
| 8/9 | Josh Fields | 3B | Sent to Minors |
| 8/9 | Horacio Ramirez | P | Traded From, Kansas City (for OF Paulo Orlando) |
| 8/9 | Jose Contreras | P | Removed From 15-Day DL, (Right elbow tendinitis) |
| 8/5 | Joe Crede | 3B | Recalled From Minors, Rehab Assignment |
| 8/5 | Adam Russell | P | Called Up from Minors |
| 8/4 | Clayton Richard | P | Sent to Minors |
| 8/3 | Jose Contreras | P | Sent to Minors, For Rehabilitation |
| 8/1 | Joe Crede | 3B | Sent to Minors, For Rehabilitation |
| 7/31 | Ken Griffey Jr. | RF | Traded From, Cincinnati (for RHP Nick Masset & 2B Danny Richar) |
| 7/27 | Jason Tyner | LF | Signed to a Minor League Contract |
| 7/26 | Ehren Wassermann | P | Called Up from Minors |
| 7/26 | Scott Linebrink | P | Placed on 15-Day DL, (Right shoulder inflammation) |
| 7/25 | Joe Crede | 3B | Placed on 15-Day DL, (Back lumbar inflammation) |
| 7/25 | Esteban Loaiza | P | Released |
| 7/25 | Josh Fields | 3B | Called Up from Minors |
| 7/25 | Esteban Loaiza | P | Recalled From Minors, Rehab Assignment |
| 7/25 | Esteban Loaiza | P | Removed From 15-Day DL, (Right shoulder inflammation) |
| 7/21 | Andrew Sisco | P | Transferred to 60-Day DL, (Left elbow surgery - out for season) |
| 7/20 | Jose Contreras | P | Placed on 15-Day DL, (Right elbow tendinitis) |
| 7/20 | D.J. Carrasco | P | Called Up from Minors |
| 7/20 | Adam Russell | P | Sent to Minors |
| 7/18 | Bobby Jenks | P | Recalled From Minors, Rehab Assignment |
| 7/18 | Bobby Jenks | P | Removed From 15-Day DL, (Left scapula bursitis) |
| 7/17 | D.J. Carrasco | P | Sent to Minors |
| 7/17 | Esteban Loaiza | P | Sent to Minors, For Rehabilitation |
| 7/16 | Pablo Ozuna | 3B | Refused Minor League Assignment - Free Agent |
| 7/14 | Bobby Jenks | P | Sent to Minors, For Rehabilitation |
| 7/9 | D.J. Carrasco | P | Purchased From Minors |
| 7/9 | Bobby Jenks | P | Placed on 15-Day DL, (Left scapula bursitis) |
| 7/8 | Paul Konerko | 1B | Removed From 15-Day DL, (Left oblique strain) |
| 7/8 | Paul Konerko | 1B | Recalled From Minors, Rehab Assignment |
| 7/8 | Pablo Ozuna | 3B | Designated for Assignment |
| 7/4 | Esteban Loaiza | P | Recalled From Minors, Rehab Assignment |
| 7/4 | Paul Konerko | 1B | Sent to Minors, For Rehabilitation |
| 6/17 | Paul Konerko | 1B | Placed on 15-Day DL, (Left oblique strain) |
| 6/17 | Dewayne Wise | CF | Purchased From Minors |
| 6/16 | Esteban Loaiza | P | Sent to Minors, For Rehabilitation |
| 6/13 | Esteban Loaiza | P | Placed on 15-Day DL, (Right shoulder inflammation) |
| 6/4 | Dewayne Wise | CF | Outrighted to Minors |
| 6/4 | Esteban Loaiza | P | Signed as Free Agent, ( 2008) |
| 6/4 | Ehren Wassermann | P | Sent to Minors |
| 5/31 | Dewayne Wise | CF | Designated for Assignment |
| 5/31 | Juan Uribe | 2B | Removed From 15-Day DL, (Strained left hamstring) |
| 5/31 | Juan Uribe | 2B | Recalled From Minors, Rehab Assignment |
| 5/29 | Danny Richar | 2B | Sent to Minors |
| 5/29 | Danny Richar | 2B | Removed From 15-Day DL, (Stress fracture in rib cage) |
| 5/29 | Danny Richar | 2B | Recalled From Minors, Rehab Assignment |
| 5/27 | Juan Uribe | 2B | Sent to Minors, For Rehabilitation |
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