Chicago Cubs
All Transactions |  | | | | Thursday, September 8th, 2033 | | Signed SP P. Conrad to a 2-year contract extension worth a total of $4,552,902. | | Signed MR Z. Elliott to a 3-year contract extension worth a total of $6,829,353. |
| Monday, August 1st, 2033 | | Placed SS J. García on the 15-day disabled list. | | Placed LF P. Swanson on the active roster. | | Activated LF P. Swanson from the disabled list. |
| Monday, July 4th, 2033 | | Placed LF P. Swanson on the 15-day disabled list. | | Placed CF R. Parker on the active roster. | | Activated CF R. Parker from the disabled list. |
| Tuesday, March 1st, 2033 | | Drafted CL F. Bautista in the 2033 first-year player draft (Round 1, Pick 15, 15th overall Pick). | | Drafted MR E. Medina in the 2033 first-year player draft (Round 2, Pick 15, 39th overall Pick). | | Drafted 2B J. Anderson in the 2033 first-year player draft (Round 3, Pick 15, 63rd overall Pick). | | Drafted SP M. Mitchell in the 2033 first-year player draft (Round 4, Pick 15, 87th overall Pick). | | Drafted CF C. Rosário in the 2033 first-year player draft (Round 5, Pick 15, 111st overall Pick). | | Drafted SP E. Corbett in the 2033 first-year player draft (Round 6, Pick 15, 135th overall Pick). | | Drafted 2B K. Parrish in the 2033 first-year player draft (Round 7, Pick 15, 159th overall Pick). | | Drafted 2B D. McVey in the 2033 first-year player draft (Round 8, Pick 15, 183rd overall Pick). | | Drafted RF A. Fuentes in the 2033 first-year player draft (Round 9, Pick 15, 207th overall Pick). | | Drafted MR G. Newman in the 2033 first-year player draft (Round 10, Pick 15, 231st overall Pick). |
| Friday, February 4th, 2033 | | Signed free agent SP J. Gallardo to a 1-year contract worth a total of $5,276,451. |
| Thursday, February 3rd, 2033 | | Signed free agent CF R. Parker to a 1-year contract worth a total of $1,276,451. | | Signed free agent SS S. Anderson to a 2-year contract worth a total of $1,952,902. | | Signed free agent SP C. Smith to a 1-year contract worth a total of $776,451. | | Signed free agent RF B. Kennedy to a 1-year contract worth a total of $576,451. | | Signed free agent SS J. García to a 2-year contract worth a total of $1,752,902. |
| Wednesday, February 2nd, 2033 | | Signed free agent MR R. Dull to a 1-year contract worth a total of $476,451. |
| Tuesday, February 1st, 2033 | | Signed free agent CL E. Diaz to a 1-year contract worth a total of $476,451. |
| Monday, January 3rd, 2033 | | Placed CL W. Harris on the 40-man roster. | | Placed CL W. Harris on the active roster. |
| Sunday, January 2nd, 2033 | | Signed free agent CL W. Harris to a 2-year contract worth a total of $5,460,000. |
| Monday, December 6th, 2032 | | Placed SP L. Rivera on the active roster. | | Activated SP L. Rivera from the disabled list. | | Placed MR M. Hernández on the active roster. | | Activated MR M. Hernández from the disabled list. |
| Tuesday, November 23rd, 2032 | | CL A. Schultz becomes a free-agent. | | RF M. Trout becomes a free-agent. | | 2B K. Spencer received a 1-year contract through automatic renewal worth a total of $276,451. | | RF M. Lewis received a 1-year contract through automatic renewal worth a total of $276,451. | | CF D. Johnson received a 1-year contract through automatic renewal worth a total of $276,451. | | MR T. Bruce becomes a free-agent. | | C T. Clark becomes a free-agent. | | 3B C. García received a 1-year contract through automatic renewal worth a total of $410,000. | | SP K. Brown becomes a free-agent. | | SS T. Wallace received a 1-year contract through automatic renewal worth a total of $276,451. | | C P. Martínez received a 1-year contract through automatic renewal worth a total of $276,451. | | LF E. Cuervo becomes a free-agent. | | RF A. Wise becomes a free-agent. | | SP J. Billingsley becomes a free-agent. | | C S. Adams becomes a free-agent. | | SS R. Ayala becomes a free-agent. | | RF A. Herrera becomes a free-agent. |
| Saturday, November 20th, 2032 | | CL J. Mcgee received a 1-year contract through arbitration worth a total of $1,875,200. | | MR M. Hernández received a 1-year contract through arbitration worth a total of $276,451. | | MR Z. Elliott received a 1-year contract through arbitration worth a total of $1,202,400. | | SP R. Craig received a 1-year contract through arbitration worth a total of $276,451. |
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