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| Friday, January 30th , 2099 |
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| Signed free agent RP Ramon Quinones to a minor league contract with a $800,000 signing bonus. |
| Signed free agent SS Ed Pollock to a 4-year contract worth a total of $64,000,000. |
| Signed RP Eric Rendleman to a 1-year contract extension worth a total of $18,200,000. |
| Promoted RP Ramon Quinones from High-A Salem to Double A Portland. |
| Demoted RP Gary Chancey from Double A Portland to Class A Greenville. |
| Wednesday, January 21st , 2099 |
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| SS Matt Palmer was claimed off waivers from Kansas City. |
| Monday, January 19th , 2099 |
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| Signed free agent SP Jeremy Wills to a minor league contract with a $300,000 signing bonus. |
| Signed free agent SP Jay Johnson to a minor league contract with a $300,000 signing bonus. |
| Signed free agent RF Dustin Spears to a minor league contract with a $300,000 signing bonus. |
| Signed free agent SP Eric in 't Veld to a minor league contract with a $200,000 signing bonus. |
| Promoted SP Jay Johnson from High-A Salem to Triple A Pawtucket. |
| Promoted RF Dustin Spears from High-A Salem to Triple A Pawtucket. |
| Promoted SP Eric in 't Veld from High-A Salem to Double A Portland. |
| Promoted SP Jeremy Wills from High-A Salem to Double A Portland. |
| Demoted RP Fred Feightner from Double A Portland to Class A Greenville. |
| Demoted RP Steve Wenzel from Double A Portland to Class A Greenville. |
| Saturday, January 17th , 2099 |
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| Promoted RP Danny Sanchez from Rookie League Boston (Rk+) to High-A Salem. |
| Friday, January 16th , 2099 |
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| Promoted RP Jim Howe from Rookie League Boston (Rk+) to Low-A Lowell. |
| Demoted RP Danny Sanchez from Low-A Lowell to Rookie League Boston (Rk+). |
| Thursday, January 15th , 2099 |
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| Sent SP Vinny Cordova from Rookie League Boston (GCL) to Rookie League Boston (Rk+). |
| Saturday, January 10th , 2099 |
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| SS Romeo Zimolo was claimed off waivers from New York. |
| Friday, January 9th , 2099 |
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| Promoted RP Omar Jimenez from Rookie League Boston (Rk+) to Low-A Lowell. |
| Demoted RP Estevan Aguilera from Low-A Lowell to Rookie League Boston (Rk+). |
| Sent RF Frank Ozaeta from Rookie League Boston (GCL) to Rookie League Boston (Rk+). |
| Sent RF Steve Kolinski from Rookie League Boston (Rk+) to Rookie League Boston (GCL). |
| Sent CF Tomas Padilla from Rookie League Boston (Rk+) to Rookie League Boston (GCL). |
| Thursday, January 8th , 2099 |
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| Signed free agent SP Giampietro Avellino to a minor league contract with a $400,000 signing bonus. |
| Signed free agent SP Alex Agramonte to a minor league contract with a $200,000 signing bonus. |
| Signed free agent CF Tim Mayfield to a minor league contract with a $200,000 signing bonus. |
| Signed free agent SS Devin Lotts to a minor league contract with a $100,000 signing bonus. |
| Signed free agent 2B Nick Barrera to a minor league contract with a $300,000 signing bonus. |
| Signed free agent SP Butch Berk to a minor league contract with a $300,000 signing bonus. |
| Signed free agent RP Sal Gomez to a minor league contract with a $300,000 signing bonus. |
| Promoted SP Butch Berk from High-A Salem to Triple A Pawtucket. |
| Promoted SP Alex Agramonte from High-A Salem to Triple A Pawtucket. |
| Promoted SP Giampietro Avellino from High-A Salem to Triple A Pawtucket. |
| Promoted 2B Nick Barrera from High-A Salem to Triple A Pawtucket. |
| Promoted RP Sal Gomez from High-A Salem to Double A Portland. |
| Promoted SS Devin Lotts from High-A Salem to Double A Portland. |
| Promoted CF Tim Mayfield from High-A Salem to Double A Portland. |
| Wednesday, January 7th , 2099 |
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| Promoted SP Joe Whaley from High-A Salem to Double A Portland. |
| Thursday, January 1st , 2099 |
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| Sent C Joe McCullough from Class A Greenville to High-A Salem. |
| Sent 1B Marco Valenzuela from Class A Greenville to High-A Salem. |
| Sent CF Nick Lewis from Rookie League Boston (GCL) to Rookie League Boston (Rk+). |
| Promoted CF Pablo Fonseca from Rookie League Boston (Rk+) to Low-A Lowell. |
| Promoted CF Jesus Becerra from Low-A Lowell to High-A Salem. |
