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| Monday, July 6th , 2099 |
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| Signed C Derick Benjamin to a 1-year contract extension worth a total of $7,500,000. |
| Sunday, July 5th , 2099 |
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| Placed 2B Paul Starmer on the Southern League 7-day injured list, retroactive to 07/04/2099. |
| Saturday, July 4th , 2099 |
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| Placed CF Stuart Thomas on the Pacific Coast League 7-day injured list, retroactive to 07/03/2099. |
| Saturday, June 27th , 2099 |
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| C Jacob Duke was claimed off waivers by Atlanta. |
| Thursday, June 25th , 2099 |
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| Optioned SP Jamie Cease to Triple A Iowa. |
| Purchased the contract of SP Kyle Dellinger from Triple A Iowa. |
| Sent 3B Rick Chamberlin from Rookie League Chicago N (AZL) to Rookie League Chicago (Rk+). |
| Sent 2B Kevin Whitcomb from Rookie League Chicago N (AZL) to Rookie League Chicago (Rk+). |
| Released 3B Alex Rios. |
| Released 3B Jesse Lombardo. |
| Released SP Donys DeHart. |
| Released LF Jessie Pegan. |
| Released SP Marco Franco. |
| Released CF Anwar Maabade. |
| Promoted 2B Kevin Whitcomb from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Promoted RP Raul Cirilo from High-A Myrtle Beach to Double A Tennessee. |
| Promoted RF Danny Thompson from High-A Myrtle Beach to Double A Tennessee. |
| Promoted SS Jake Hendrickson from High-A Myrtle Beach to Double A Tennessee. |
| Promoted 2B Paul Starmer from High-A Myrtle Beach to Double A Tennessee. |
| Promoted C Mike Finlayson from High-A Myrtle Beach to Double A Tennessee. |
| Promoted RP Raul Cirilo from Double A Tennessee to Triple A Iowa. |
| Optioned SP Jamie Cease to Triple A Iowa. |
| Purchased the contract of SP Kyle Dellinger from Triple A Iowa. |
| Tuesday, June 16th , 2099 |
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| Drafted 3B Rick Chamberlin in the 2099 first-year player draft (Round 1, Pick 24, 24th overall pick). |
| Drafted SP Aaron Baker in the 2099 first-year player draft (Round 2, Pick 19, 57th overall pick). |
| Drafted CF Billy O'Neill in the 2099 first-year player draft (Round 3, Pick 23, 85th overall pick). |
| Drafted SP Kyle Alexander in the 2099 first-year player draft (Round 5, Pick 25, 145th overall pick). |
| Drafted SP Devlin Wilcox in the 2099 first-year player draft (Round 6, Pick 25, 175th overall pick). |
| Drafted RP Cruz Salas in the 2099 first-year player draft (Round 7, Pick 25, 205th overall pick). |
| Drafted C Sam Oden in the 2099 first-year player draft (Round 8, Pick 25, 235th overall pick). |
| Drafted CF Emilio Duran in the 2099 first-year player draft (Round 9, Pick 25, 265th overall pick). |
| Drafted SP Ryan Perry in the 2099 first-year player draft (Round 10, Pick 25, 295th overall pick). |
| Drafted SP Kevin Goins in the 2099 first-year player draft (Round 11, Pick 25, 325th overall pick). |
| Drafted CF Sean Kelley in the 2099 first-year player draft (Round 12, Pick 25, 355th overall pick). |
| Drafted RF Chris Wildes in the 2099 first-year player draft (Round 13, Pick 25, 385th overall pick). |
| Drafted C Scott Lueth in the 2099 first-year player draft (Round 14, Pick 25, 415th overall pick). |
| Drafted SS Jon Bushby in the 2099 first-year player draft (Round 15, Pick 25, 445th overall pick). |
| Drafted RF Larry Gregory in the 2099 first-year player draft (Round 16, Pick 25, 475th overall pick). |
| Drafted SP Luis Silva in the 2099 first-year player draft (Round 17, Pick 25, 505th overall pick). |
| Drafted SS Scott McCall in the 2099 first-year player draft (Round 18, Pick 25, 535th overall pick). |
| Drafted LF Ryan Blair in the 2099 first-year player draft (Round 19, Pick 25, 565th overall pick). |
| Drafted LF Tom Quinby in the 2099 first-year player draft (Round 20, Pick 25, 595th overall pick). |
| Drafted 3B Jaden Spencer in the 2099 first-year player draft (Round 21, Pick 25, 625th overall pick). |
| Drafted RF David Soto in the 2099 first-year player draft (Round 22, Pick 25, 655th overall pick). |
| Drafted SP Eddie Wittenstein in the 2099 first-year player draft (Round 23, Pick 25, 685th overall pick). |
| Drafted LF Jake Hagy in the 2099 first-year player draft (Round 24, Pick 25, 715th overall pick). |
| Drafted 3B Jesse Lombardo in the 2099 first-year player draft (Round 25, Pick 25, 745th overall pick). |
| Sunday, June 14th , 2099 |
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| Signed free agent CL Raul Cirilo to a minor league contract with a $250,000 signing bonus. |
| Signed free agent SP Luis Reyes to a 1-year contract worth a total of $50,100,000. |
| Optioned RP Jamie DeCiantis to Triple A Iowa. |
| Placed SP Luis Reyes on the active roster. |
| C Jacob Duke was designated for assignment and placed on waivers. |
| Placed C Derick Benjamin on the active roster. |
| Activated C Derick Benjamin from the 60-day injured list. |
| Sent RP Kyle Dellinger to Triple A Iowa for injury rehab. |
| Optioned RP Jamie DeCiantis to Triple A Iowa. |
| Placed SP Luis Reyes on the secondary (40-man) roster. |
| Placed SP Luis Reyes on the active roster. |
| C Jacob Duke was designated for assignment and placed on waivers. |
| Placed C Derick Benjamin on the secondary (40-man) roster. |
| Placed C Derick Benjamin on the active roster. |
| Activated C Derick Benjamin from the 60-day injured list. |
| Sent RP Kyle Dellinger to Triple A Iowa for injury rehab. |
| Released 3B Angel Lagunas. |
| Promoted C Mike Hubbard from Rookie League Chicago N (AZL) to Low-A Eugene. |
| Promoted 2B Bobby Ayala from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Promoted CF Hector Camarillo from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Promoted CF Aiden Byrd from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Sent LF Jessie Pegan from Rookie League Chicago N (AZL) to Rookie League Chicago (Rk+). |
| Sent CF Felipe Fernandez from Rookie League Chicago N (AZL) to Rookie League Chicago (Rk+). |
| Demoted C Sean Ryan from Low-A Eugene to Rookie League Chicago (Rk+). |
| Sent 2B Paul Starmer from Class A South Bend to High-A Myrtle Beach. |
| Sent SS Mike Bryant from Class A South Bend to High-A Myrtle Beach. |
| Sent RF Vic Payne from Class A South Bend to High-A Myrtle Beach. |
| Promoted SP Matt Helsen from High-A Myrtle Beach to Double A Tennessee. |
| Wednesday, June 3rd , 2099 |
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| Optioned SS Ryan Helsel to Triple A Iowa. |
| Placed SS Brent Griffin on the active roster. |
| Activated SS Brent Griffin from the injured list. |
| Optioned RP Ron Boone to Triple A Iowa. |
| Purchased the contract of RP Ron Boone from Triple A Iowa. |
| Signed Scouting Director Ben Spring to a 5-year contract extension. |
| Sent SP Ron Dutton from Class A South Bend to High-A Myrtle Beach. |
| Optioned SS Ryan Helsel to Triple A Iowa. |
| Placed SS Brent Griffin on the active roster. |
| Activated SS Brent Griffin from the injured list. |
| Optioned RP Ron Boone to Triple A Iowa. |
| Purchased the contract of RP Ron Boone from Triple A Iowa. |
| Signed Scouting Director Ben Spring to a 5-year contract extension. |
| Monday, June 1st , 2099 |
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| Placed 3B David Green on the Midwest League 7-day injured list, retroactive to 05/31/2099. |
| Friday, May 29th , 2099 |
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| Placed 2B Paul Starmer on the restricted list. |
| Saturday, May 23rd , 2099 |
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| Placed RP Kyle Dellinger on the 15-day injured list. |
| Placed SP Aaron Hosey on the active roster. |
| Activated SP Aaron Hosey from the injured list. |
| Placed RP Kyle Dellinger on the 15-day injured list. |
| Placed SP Aaron Hosey on the active roster. |
| Activated SP Aaron Hosey from the injured list. |
| Friday, May 22nd , 2099 |
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| Placed RF Jim Norris on the Southern League 7-day injured list, retroactive to 05/21/2099. |
| Tuesday, May 12th , 2099 |
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| Placed SS Brent Griffin on the 10-day injured list, retroactive to 05/09/2099. |
| Purchased the contract of SS Ryan Helsel from Triple A Iowa. |
| Optioned CF Stuart Thomas to Triple A Iowa. |
| Placed RP Jarred Karr on the active roster. |
| Activated RP Jarred Karr from the injured list. |
| Placed SS Brent Griffin on the 10-day injured list, retroactive to 05/09/2099. |
| Placed SS Ryan Helsel on the secondary (40-man) roster. |
| Purchased the contract of SS Ryan Helsel from Triple A Iowa. |
| Promoted CF Craig Bennett from Double A Tennessee to Triple A Iowa. |
| Promoted RF Ryan Adkins from High-A Myrtle Beach to Triple A Iowa. |
| Promoted 2B Erik Bazan from High-A Myrtle Beach to Triple A Iowa. |
| Optioned CF Stuart Thomas to Triple A Iowa. |
| Placed RP Jarred Karr on the active roster. |
| Activated RP Jarred Karr from the injured list. |
| Saturday, May 9th , 2099 |
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| SS Ryan Helsel did not elect for free agency and will remain in the Chicago organization. |
| Friday, May 1st , 2099 |
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| Signed free agent RF Ryan Adkins to a minor league contract with a major league option. |
| Signed free agent 2B Erik Bazan to a minor league contract with a major league option. |
| Placed SP Aaron Hosey on the 15-day injured list, retroactive to 04/28/2099. |
| Purchased the contract of CF Devin Williams from Triple A Iowa. |
| Placed SP Aaron Hosey on the 15-day injured list, retroactive to 04/28/2099. |
| Purchased the contract of CF Devin Williams from Triple A Iowa. |
| Monday, April 20th , 2099 |
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| Placed RP Jarred Karr on the 15-day injured list, retroactive to 04/17/2099. |
| Purchased the contract of SP Ron Boone from Triple A Iowa. |
| Optioned 3B Jaylin Tillman to Triple A Iowa. |
| Purchased the contract of 3B Howie Seabolt from Triple A Iowa. |
| Placed RP Jarred Karr on the 15-day injured list, retroactive to 04/17/2099. |
| Purchased the contract of SP Ron Boone from Triple A Iowa. |
| Optioned 3B Jaylin Tillman to Triple A Iowa. |
| Purchased the contract of 3B Howie Seabolt from Triple A Iowa. |
| Sent CF Craig Bennett from Class A South Bend to High-A Myrtle Beach. |
| Released CF Nate Morgan. |
| Promoted CF Craig Bennett from High-A Myrtle Beach to Double A Tennessee. |
| Promoted CF Jeremy Piland from Double A Tennessee to Triple A Iowa. |
| Thursday, April 9th , 2099 |
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| Placed SP Ron Payne on the 60-day injured list. |
| Optioned 3B Howie Seabolt to Triple A Iowa. |
| Optioned CF Devin Williams to Triple A Iowa. |
| Placed SP Ron Payne on the 60-day injured list. |
| Optioned 3B Howie Seabolt to Triple A Iowa. |
| Optioned CF Devin Williams to Triple A Iowa. |
| Promoted CF Jeremy Piland from High-A Myrtle Beach to Double A Tennessee. |
| Promoted international complex member SS Luis Martinez to Rookie League Chicago N (AZL). |
| Promoted international complex member SP Jorge Mendez to Rookie League Chicago (Rk+). |
| Promoted international complex member SS Miguel Zepeda to Rookie League Chicago (Rk+). |
| Promoted SS Ryan Helsel from Rookie League Chicago N (AZL) to Triple A Iowa. |
| Sent C Scott Baker from Rookie League Chicago N (AZL) to Rookie League Chicago (Rk+). |
| Promoted RF Bobby Sandoval from Rookie League Chicago N (AZL) to Low-A Eugene. |
| Sent CF Brian Young from Rookie League Chicago N (AZL) to Rookie League Chicago (Rk+). |
| Demoted SP Jeff Anderson from Low-A Eugene to Rookie League Chicago (Rk+). |
| Promoted C Jose Madrid from Low-A Eugene to Class A South Bend. |
| Promoted 2B Bill Hubble from Low-A Eugene to Class A South Bend. |
| Promoted SS John Grundy from Low-A Eugene to Class A South Bend. |
| Promoted LF Joel Gosselin from Low-A Eugene to Class A South Bend. |
| Promoted LF Lance Corsi from Low-A Eugene to Class A South Bend. |
| Promoted 2B Chad Allen from Low-A Eugene to Class A South Bend. |
| Promoted 2B Brian Newman from Low-A Eugene to Class A South Bend. |
| Promoted SS Dan Pattullo from Low-A Eugene to Class A South Bend. |
| Sent 2B Phil Robbins from Class A South Bend to High-A Myrtle Beach. |
| Friday, March 27th , 2099 |
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| Signed international amateur SP Victor Atencio out of Dominican Republic to a minor league contract with a $2,300,000 signing bonus. |
| Optioned CF John Borchardt to Triple A Iowa. |
| Optioned CF Jonathan Stooksberry to Triple A Iowa. |
| Optioned SP Brandon Banks to High-A Myrtle Beach. |
| Optioned RP Tim Linden to Triple A Iowa. |
| Optioned RP Ron Boone to Triple A Iowa. |
| Optioned RP Joe Edwards to Double A Tennessee. |
| Optioned CF John Borchardt to Triple A Iowa. |
| Optioned CF Jonathan Stooksberry to Triple A Iowa. |
| Optioned SP Brandon Banks to High-A Myrtle Beach. |
| Optioned RP Tim Linden to Triple A Iowa. |
| Optioned RP Ron Boone to Triple A Iowa. |
| Optioned RP Joe Edwards to Double A Tennessee. |
| Demoted LF Ryan Ogle from Triple A Iowa to High-A Myrtle Beach. |
| Monday, March 16th , 2099 |
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| Signed international amateur RF Ruben Cardenas out of Dominican Republic to a minor league contract with a $21,700,000 signing bonus. |
| Optioned SP Vince Roberts to Triple A Iowa. |
| Optioned SP Mike Wallace to High-A Myrtle Beach. |
| Optioned SP Bill Burroughs to High-A Myrtle Beach. |
| Optioned LF Ryan Ogle to Triple A Iowa. |
| Optioned SP Vince Roberts to Triple A Iowa. |
| Optioned SP Mike Wallace to High-A Myrtle Beach. |
| Optioned SP Bill Burroughs to High-A Myrtle Beach. |
| Optioned LF Ryan Ogle to Triple A Iowa. |
| Thursday, March 5th , 2099 |
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| Purchased the contract of SP Brandon Banks from High-A Myrtle Beach. |
| Purchased the contract of SP Bill Burroughs from High-A Myrtle Beach. |
| Purchased the contract of CF John Borchardt from Double A Tennessee. |
| Purchased the contract of SP Vince Roberts from Triple A Iowa. |
| Purchased the contract of SP Mike Wallace from Class A South Bend. |
| Purchased the contract of SP Joe Edwards from Double A Tennessee. |
| Purchased the contract of SP Ron Boone from Triple A Iowa. |
| Purchased the contract of LF Ryan Ogle from High-A Myrtle Beach. |
| Invited non-roster SP Matt Helsen to Spring Training camp. |
| Assigned SP Matt Helsen from Spring Training camp to High-A Myrtle Beach. |
| Placed C Derick Benjamin on the 60-day injured list. |
| Invited non-roster SP Matt Helsen to Spring Training camp. |
| Assigned SP Matt Helsen from Spring Training camp to High-A Myrtle Beach. |
| Placed C Derick Benjamin on the 60-day injured list. |
| Saturday, February 21st , 2099 |
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| Signed free agent SS Ryan Helsel to a minor league contract with a major league option. |
| Monday, January 19th , 2099 |
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| Signed free agent SS Chris Downs to a 2-year contract worth a total of $28,000,000. |
| Traded $1 in cash to the Toronto Blue Jays, getting $1 in cash and $9,000,000 in international amateur bonus pool room in return. |
| Placed SS Chris Downs on the active roster. |
| Placed SS Chris Downs on the secondary (40-man) roster. |
| Placed SS Chris Downs on the active roster. |
| Promoted SP Ron Dutton from Low-A Eugene to Class A South Bend. |
| Promoted 3B David Green from Low-A Eugene to Class A South Bend. |
| Promoted 2B Paul Starmer from Low-A Eugene to Class A South Bend. |
| Promoted CF Craig Bennett from Low-A Eugene to Class A South Bend. |
| Promoted 3B Michael Guimond from Low-A Eugene to Class A South Bend. |
| Promoted 3B Tristan Greenwood from Low-A Eugene to Class A South Bend. |
| Promoted 2B Jim Worsham from Low-A Eugene to Class A South Bend. |
| Promoted CF Chris Thompkins from Low-A Eugene to Class A South Bend. |
| Promoted C Jason Hassinger from Low-A Eugene to Class A South Bend. |
| Promoted SP Jeff Anderson from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Promoted C Sean Ryan from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Promoted CF Marcus Phelps from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Promoted CF Vicente Anastacio from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Promoted CF Hector Camarillo from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Promoted SS Mike Brown from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Promoted C Eric Colyer from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Promoted LF Ken Drake from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Demoted CF Hector Camarillo from Low-A Eugene to Rookie League Chicago (Rk+). |
| Promoted 1B Kevin Keller from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Promoted RF Chris Singleton from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Promoted RF Joe Waddell from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Promoted CF Hector Camarillo from Rookie League Chicago (Rk+) to Low-A Eugene. |
| Demoted CF Hector Camarillo from Low-A Eugene to Rookie League Chicago (Rk+). |
| Promoted 3B Danny Morales from Rookie League Chicago N (AZL) to Low-A Eugene. |
| Promoted C Jake Allen from Rookie League Chicago N (AZL) to Low-A Eugene. |
| Promoted RF Nick Keller from Rookie League Chicago N (AZL) to Low-A Eugene. |
| Promoted 3B Angel Lagunas from Rookie League Chicago N (AZL) to Low-A Eugene. |
| Promoted CF Anwar Maabade from Rookie League Chicago N (AZL) to Low-A Eugene. |
| Promoted LF Leo Rivera from Rookie League Chicago N (AZL) to Low-A Eugene. |
| Demoted 3B Angel Lagunas from Low-A Eugene to Rookie League Chicago (Rk+). |
| Promoted SS Mike Carlson from Class A South Bend to Double A Tennessee. |
