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| Tuesday, October 26th, 1999 |
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| Bench Coach Johnny Bench leaves the team, his contract was not renewed. |
| Hitting Coach Paul Blair leaves the team, his contract was not renewed. |
| Saturday, September 11th, 1999 |
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| Placed SP Archie Campbell on the 60-day injured list. |
| Purchased the contract of RP Zeke Spruill from Triple A Rancho Cucamonga. |
| Thursday, September 9th, 1999 |
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| Placed SP John Halama on the 13-day injured list, retroactive to 09/08/1999. |
| Thursday, September 2nd, 1999 |
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| Traded 30-year-old starting pitcher Dixie Leverett and 30-year-old starting pitcher Harry C. Harper to the Tampon Bay Pussies, getting 30-year-old minor league starting pitcher Armando Reynoso and 36-year-old minor league starting pitcher Toshihide Hatafuku in return. |
| Purchased the contract of RP Ed Hughes from Triple A Rancho Cucamonga. |
| Friday, August 20th, 1999 |
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| Transferred RF Bill Nicholson to the 60-day IL. |
| Recalled RP Kyle Gibson from Triple A Rancho Cucamonga. |
| Recalled RP Frank Wyman from Triple A Rancho Cucamonga. |
| Recalled RP John Halama from Triple A Rancho Cucamonga. |
| Recalled C Chris Fulmer from Triple A Rancho Cucamonga. |
| Recalled RF Jim Barbieri from Triple A Rancho Cucamonga. |
| Recalled RP Archie Campbell from Triple A Rancho Cucamonga. |
| Recalled 2B Jace Peterson from Triple A Rancho Cucamonga. |
| Recalled 2B Luis Alvarado from Triple A Rancho Cucamonga. |
| Recalled C Terry Humphrey from Triple A Rancho Cucamonga. |
| Thursday, August 12th, 1999 |
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| Traded 37-year-old starting pitcher Lefty Grove to the Houston Black Aces, getting 30-year-old starting pitcher Harry C. Harper in return. |
| Traded 25-year-old starting pitcher Bobby J Jones, 31-year-old center fielder Wendell Magee and 25-year-old minor league reliever Chris R Young to the New York Yankees, getting 28-year-old starting pitcher Sonny Siebert, 31-year-old minor league catcher Harry Chiti, 27-year-old reliever Jack Hallett and 23-year-old right fielder Trot Nixon in return. |
| Placed SP Sonny Siebert on the active roster. |
| Placed RP Harry C. Harper on the active roster. |
| Placed C Harry Chiti on the active roster. |
| Demoted C Terry Humphrey to Triple A Rancho Cucamonga. |
| Placed CF Trot Nixon on the active roster. |
| Sent RP Ed Hughes to Triple A Rancho Cucamonga for injury rehab. |
| Demoted C Chris Fulmer to Triple A Rancho Cucamonga. |
| Placed RP Jack Hallett on the active roster. |
| Placed RP Jack Hallett on the 60-day injured list. |
| Purchased the contract of C Chris Fulmer from Triple A Rancho Cucamonga. |
| Traded 28-year-old starting pitcher Sonny Siebert to the Houston Black Aces, getting 22-year-old minor league reliever Frank Wyman and 31-year-old minor league catcher Dick Brown in return. |
| Placed C Dick Brown on the active roster. |
| Assigned RP Frank Wyman to Triple A Rancho Cucamonga. |
| Demoted C Chris Fulmer to Triple A Rancho Cucamonga. |
| Placed CF Jaycob Brugman on the 60-day injured list. |
| Tuesday, July 20th, 1999 |
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| Assigned RP Zeke Spruill to Triple A Rancho Cucamonga. |
| Monday, July 12th, 1999 |
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| Activated 3B Harry Steinfeldt from the injured list. |
| Purchased the contract of RP Allan Anderson from Triple A Rancho Cucamonga. |
| Recalled CF Daryl Boston from Triple A Rancho Cucamonga. |
| Demoted RP John Halama to Triple A Rancho Cucamonga. |
| Demoted RF Jim Barbieri to Triple A Rancho Cucamonga. |
| Demoted 2B Jace Peterson to Triple A Rancho Cucamonga. |
| Tuesday, June 29th, 1999 |
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| Traded 33-year-old closer Bob Locker to the New York Yankees, getting 22-year-old shortstop Lonny Frey in return. |
| Placed 3B Harry Steinfeldt on the 13-day injured list, retroactive to 06/14/1999. |
| Activated SP Lefty Grove from the injured list. |
| Purchased the contract of RP Phil Leftwich from Triple A Rancho Cucamonga. |
| Recalled SS George McBride from Triple A Rancho Cucamonga. |
| Demoted RP Kyle Gibson to Triple A Rancho Cucamonga. |
| Demoted 2B Luis Alvarado to Triple A Rancho Cucamonga. |
| Traded 35-year-old closer Frank Browning and 27-year-old left fielder Johnny Mokan to the Tampon Bay Pussies, getting 33-year-old reliever Heathcliff Slocumb and 32-year-old right fielder Jackie Bradley in return. |
| Placed RP Heathcliff Slocumb on the active roster. |
| Placed RF Jackie Bradley on the active roster. |
| Sunday, June 20th, 1999 |
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| Placed RP John Halama on the active roster. |
| Activated RP John Halama from the injured list. |
| Sunday, June 13th, 1999 |
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| Demoted RF Jim Barbieri to Triple A Rancho Cucamonga. |
| Placed RF Bill Nicholson on the 13-day injured list, retroactive to 06/12/1999. |
| Purchased the contract of RF Jim Barbieri from Triple A Rancho Cucamonga. |
| Friday, June 4th, 1999 |
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| Placed SP Lefty Grove on the 13-day injured list, retroactive to 05/14/1999. |
| Placed C Pop Schriver on the 60-day injured list. |
| Purchased the contract of RP Kyle Gibson from Triple A Rancho Cucamonga. |
| Tuesday, May 25th, 1999 |
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| Placed RP John Halama on the 13-day injured list, retroactive to 05/22/1999. |
| Placed RF Bill Nicholson on the active roster. |
| Activated RF Bill Nicholson from the injured list. |
| Demoted RP Zeke Spruill to Triple A Rancho Cucamonga. |
| Thursday, May 20th, 1999 |
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| Signed 1B George C Scott to a 1-year contract extension worth a total of $49,000. |
| Monday, May 17th, 1999 |
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| Signed SS Luis Aparicio to a 1-year contract extension worth a total of $45,000. |
| Friday, May 14th, 1999 |
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| Signed SP Lefty Grove to a 1-year contract extension worth a total of $61,000. |
| Thursday, May 13th, 1999 |
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| Signed C Pop Schriver to a 1-year contract extension worth a total of $63,000. |
| Friday, April 9th, 1999 |
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| Assigned RP Allan Anderson to Triple A Rancho Cucamonga. |
| Assigned 3B Jolbert Cabrera to Triple A Rancho Cucamonga. |
| Placed RP Ed Hughes on the 60-day injured list. |
| Thursday, February 18th, 1999 |
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| Traded 23-year-old center fielder Kenny Lofton to the Tampon Bay Pussies, getting 29-year-old third baseman George C Scott in return. |
| Placed 1B George C Scott on the active roster. |
