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Monday, December 13th , 1999
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Signed free agent C Ron Hassey to a 5-year contract worth a total of $37,500,000.
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Tuesday, November 23rd , 1999
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CL Greg Bollo received a 1-year contract through arbitration worth a total of $3,417,000.
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RP Paul Fry received a 1-year contract through arbitration worth a total of $1,300,000.
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RP Brad Halsey received a 1-year contract through arbitration worth a total of $1,139,970.
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SP Clyde King received a 1-year contract through arbitration worth a total of $2,000,000.
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RP Max Macon received a 1-year contract through arbitration worth a total of $2,000,000.
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RP Dave Beard received a 1-year contract through arbitration worth a total of $800,000.
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RP MacKenzie Gore received a 1-year contract through arbitration worth a total of $1,214,340.
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RP Fred Baczewski received a 1-year contract through arbitration worth a total of $900,000.
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C Harry Chiti received a 1-year contract through arbitration worth a total of $800,000.
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SP Mike Fiers received a 1-year contract through arbitration worth a total of $5,863,000.
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3B Greg Dobbs received a 1-year contract through arbitration worth a total of $700,000.
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RP Johan Oviedo received a 1-year contract through arbitration worth a total of $1,353,600.
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3B Mike Shannon received a 1-year contract through arbitration worth a total of $1,600,000.
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Sunday, November 7th , 1999
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Signed 2B Angel Berroa to a 4-year contract extension worth a total of $30,000,000.
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Saturday, August 28th , 1999
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Placed SS Gair Allie on the restricted list.
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Saturday, June 19th , 1999
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Placed CF Dave Martinez on the MLB Triple A 7-day injured list, retroactive to 06/18/1999.
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Thursday, May 13th , 1999
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Signed free agent SP Roy Oswalt to a 1-year contract worth a total of $10,600,000.
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Wednesday, May 5th , 1999
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Placed CF Dave Martinez on the MLB Triple A 7-day injured list, retroactive to 05/04/1999.
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Sunday, May 2nd , 1999
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SS Joe Boley did not elect for free agency and will remain in the Boston organization.
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2B Eddie Miller did not elect for free agency and will remain in the Boston organization.
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SS Damian Jackson did not elect for free agency and will remain in the Boston organization.
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Tuesday, January 12th , 1999
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Drafted LF Bobby Scales in the 1998 first-year player draft (Round 4, Pick 5, 65th overall pick).
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Drafted 2B Lou Stringer in the 1998 first-year player draft (Round 4, Pick 12, 72nd overall pick).
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Drafted SS Gair Allie in the 1998 first-year player draft (Round 5, Pick 12, 92nd overall pick).
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Drafted 3B Bill Andrus in the 1998 first-year player draft (Round 6, Pick 12, 112nd overall pick).
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Thursday, January 7th , 1999
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Signed free agent SS Damian Jackson to a minor league contract with a major league option.
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