Transactions 2009 Through Monday, May 18th
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Trades:
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| Team Name | Replaced | Picked Up |
| Priory of Yawkey Way | Released - Gavin Floyd | Rick Porcello |
| Winged Buffalo | Released - Justin Masterson | Jorge De La Rosa |
| Reversal of Fortune | DL - Ryan Ludwick | Eric Byrnes |
| WWEDD? | Released - Kyle Farnsworth | CJ Wilson |
| Iron Men | Released - Dexter Fowler | Gerardo Parra |
| The Bigg Doggs | DL - Jesus Flores | Nick Hundley |
| Priory of Yawkey Way | Released - David Aardsma | Activated - Brandon Morrow |
| Winged Buffalo | DL - Conor Jackson | Casey Blake |
| Winged Buffalo | Released - Luke Hochevar | Manny Parra |
| Reversal of Fortune | Released - Mike Aviles | No Open Spot |
| Reversal of Fortune | Released - Scott Richmond | Activated - Chris Volstad |
| WWEDD? | Released - Josh Anderson | Fred Lewis |
| Iron Men | Released - Mike Fontenot | Melvin Mora |
| The Bigg Doggs | Released - Juan Cruz | Activated - Matt Capps |
| Camel Jockeys | DL - Kevin Youkilis | Activated - Chris Young |
| Camel Jockeys | Released - Trevor Cahill | No Open Spot |
| Camel Jockeys | Minors - Ricky Romero | No Open Spot |
| BALCO Bombers | DL - Pat Burrell | Activated - Stephen Drew |
| I Like Big Bunts | DL - Frank Francisco | Joel Hanrahan |
| I Like Big Bunts | Released - Joel Zumaya | No Open Spot |
| Iron Men | DL - Rickie Weeks | Akinori Iwamura |
| A.C.L. | Released - Andruw Jones | Activated - Magglio Ordonez |
| A.C.L. | DL - Carlos Delgado | Fernando Tatis |
| Iron Men | Released - Andy Pettitte | Activated - Ryan Madson |
| Non - Smokers | Released - Scott Rolen | Activated - Derrek Lee |
| Non - Smokers | Released - David Ortiz | No Open Spot |
| Winged Buffalo | Released - Brett Anderson | No Open Spot |
| A.C.L. | Released - Phil Hughes | No Open Spot |
| Priory of Yawkey Way | Released - Kevin Kouzmanoff | No Open Spot |
| Reserve Moves | ||
| Priory of Yawkey Way | Reserved - Erik Bedard | Rich Hill |
| Sultans of Swat | Reserved - Scott Baker | Matt Harrison |
| A.C.L. | Reserved - Glen Perkins | Activated - John Lackey |
| Camel Jockeys | Reserved - Sean Marshall | Shairon Martis |
| Camel Jockeys | Reserved - Jonathan Sanchez | Scott Feldman |
| Non - Smokers | Reserved - Carlos Quentin | Milton Bradley |