Transactions 2009 Through Monday, May 25th
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Trades: Winged Buffalo traded Brian Roberts and Kevin Millwood to The Bigg Doggs for Josh Johnson and Denard Span. BALCO Bombers traded Stephen Drew to the Winged Buffalo for Denard Span and Conor Jackson.
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| Team Name | Replaced | Picked Up |
| Priory of Yawkey Way | Released - Ryan Spilborghs | Michael Cuddyer |
| Camel Jockeys | Released - Shairon Martis | Dontrelle Willis |
| Reversal of Fortune | Minors - Brett Cecil | Kyle Lohse |
| WWEDD? | Minors - Travis Snider | David DeJesus |
| Iron Men | Released - Aaron Bailey | David Aardsma |
| The Bigg Doggs | Released - Nick Hundley | Dioner Navarro |
| Priory of Yawkey Way | Released - Brandon Morrow | Kenshin Kawakami |
| Reversal of Fortune | Minors - Ricky Nolasco | Scott Richmond |
| Priory of Yawkey Way | Released - Emmanuel Burriss | Orlando Cabrera |
| Reversal of Fortune | DL - Chris Ianettta | Omir Santos |
| I Like Big Bunts | DL - Rich Harden | Activated - Chris Carpenter |
| I Like Big Bunts | Released - Octavio Dotel | Activated - Frank Francisco |
| A.C.L. | Released - Fernando Tatis | Kevin Kouzmanoff |
| I Like Big Bunts | DL - Elijah Dukes | Cody Ross |
| Priory of Yawkey Way | DL - Scott Kazmir | Activated - Erik Bedard |
| A.C.L. | Released - Barry Zito | Doug Davis |
| Iron Men | DL - Akinori Iwamura | Scott Schumaker |
| Winged Buffalo | Released - Manny Parra | Activated - Daisuke Matsusaka |
| Non - Smokers | Released - Milton Bradley | Activated - Carlos Quentin |
| Non - Smokers | Released - Jarrod Washburn | Activated - Ervin Santana |
| BALCO Bombers | Released - B.J. Ryan | No Open Spot |
| Camel Jockeys | Released - Sean Marshall | No Open Spot |
| Camel Jockeys | DL - Edinson Volquez | Gavin Floyd |
| Camel Jockeys | Released - Scott Feldman | Activated - Jonathan Sanchez |
| A.C.L. | Released - Glen Perkins | No Open Spot |
| Sultans of Swat | DL - Troy Percival | Activated - Scott Baker |
| Reserve Moves | ||
| Winged Buffalo | Reserved - Colby Rasmus | David Ortiz |
| Camel Jockeys | Reserved - Chris Young (AZ) | Activated - Kevin Youkilis |
| Iron Men | Reserved - Yunel Escobar | Ben Zobrist |
| The Bigg Doggs | Reserved - Nyjer Morgan | Dexter Fowler |
| Non - Smokers | Reserved - Pablo Sandoval | Scott Rolen |
| BALCO Bombers | Reserved - Todd Wellemeyer | Dan Wheeler |
| Camel Jockeys | Reserved - Jose Reyes | Edgar Renteria |