| Sunday, December 30th, 2018 |
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| Signed free agent CF Zach Hutchinson to a 5-year contract worth a total of $91,000,000. |
| Saturday, December 1st, 2018 |
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| Signed free agent MR Gordon Brown to a 1-year contract worth a total of $1,100,000. | | Signed free agent MR Lúcio Tapia to a 1-year contract worth a total of $900,000. | | Signed free agent SP Nam-cheol Chong to a 5-year contract worth a total of $92,000,000. | | Traded 29-year-old starting pitcher Olivier Beaudoin, 22-year-old minor league first baseman Derek Ramsey and $650,000 in cash to the Chicago Machine, getting 25-year-old minor league starting pitcher Bartolo Romo, 24-year-old minor league starting pitcher Mario Chávez, 31-year-old shortstop Rafael Salas and 20-year-old minor league center fielder Don Keating in return. | | Placed SP Nam-cheol Chong on the active roster. | | Placed MR Gordon Brown on the active roster. | | Placed MR Lúcio Tapia on the active roster. | | Placed SS Rafael Salas on the active roster. | | Recalled SP Robert Reeves from Triple A Waba. | | Purchased the contract of SP Bartolo Romo from Triple A Waba. | | Purchased the contract of SP Soh Suzuki from Triple A Waba. | | Demoted SP Bartolo Romo to Triple A Waba. | | Drafted MR Alonso Gallardo in the 2018 Rule 5 Draft (Round 1, Pick 23, 23rd overall Pick), from the Orlando Calrissian. |
| Tuesday, November 20th, 2018 |
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| SP Manuel Medina becomes a free-agent. | | LF Keith Bailey received a 1-year contract through automatic renewal worth a total of $400,000. | | C Kyuso Fujita becomes a free-agent. | | C Mark Hebert received a 1-year contract through automatic renewal worth a total of $400,000. | | MR Jesús Deleón becomes a free-agent. | | MR Félix Rivera received a 1-year contract through automatic renewal worth a total of $400,000. | | SP Lorenzo López received a 1-year contract through automatic renewal worth a total of $400,000. | | CF Júlio Hernández received a 1-year contract through automatic renewal worth a total of $400,000. | | LF Cooper Newell becomes a free-agent. | | CL Daniel Morris becomes a free-agent. |
| Tuesday, November 13th, 2018 |
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| Signed SP Olivier Beaudoin to a 4-year contract extension worth a total of $38,000,000. |
| Friday, November 9th, 2018 |
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| Signed 3B José Padilla to a 2-year contract extension worth a total of $2,800,000. |
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