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| Wednesday, October 30th , 2019 |
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| Drafted CF Jay Clinkscales in the 2019 first-year player draft (Round 1, Pick 2, 2nd overall pick). |
| Drafted 3B Josh Winger in the 2019 first-year player draft (Round 5, Pick 2, 74th overall pick). |
| Thursday, August 8th , 2019 |
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| Signed - Bubba Ostendorf to a 2-year contract extension. |
| Wednesday, May 1st , 2019 |
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| Promoted RP Heinz Brown to Major League Chicago. |
| Promoted SP Ben Scarbrough to Major League Chicago. |
| Promoted RP Jadon McClendon to Major League Chicago. |
| Promoted RP Joe Nord to Major League Chicago. |
| Promoted RP Jon Naugle to Major League Chicago. |
| Promoted C Robert DeRosa to Major League Chicago. |
| Promoted 2B Toby Mazure to Major League Chicago. |
| Promoted SP Makai Buckner to Major League Chicago. |
