| | | | | | | | | | | _Cubs.png) | Major Transactions |
| | | | Wednesday, September 21st, 1966 | | Signed 1B E. Banks to a 1-year contract extension worth a total of $66,000. |
| Tuesday, September 6th, 1966 | | Signed CF L. Brock to a 3-year contract extension worth a total of $2,886,000. |
| Wednesday, December 15th, 1965 | | Placed SP G. Brunet on the active roster. | | Placed 2B F. Bolling on the active roster. |
| Monday, December 6th, 1965 | | Signed free agent SP G. Brunet to a 2-year contract worth a total of $210,000. |
| Saturday, December 4th, 1965 | | Signed free agent 2B F. Bolling to a 1-year contract worth a total of $50,000. |
| Tuesday, November 16th, 1965 | | C J. Grote received a 1-year contract through automatic renewal worth a total of $24,774. | | 1B W. Parker received a 1-year contract through automatic renewal worth a total of $24,774. | | MR J. Cullen received a 1-year contract through automatic renewal worth a total of $24,774. | | 2B D. Johnson received a 1-year contract through automatic renewal worth a total of $24,774. | | LF T. Reynolds received a 1-year contract through automatic renewal worth a total of $24,774. | | C E. Bailey becomes a free-agent. | | SP F. Jenkins received a 1-year contract through automatic renewal worth a total of $24,774. | | SP S. Blass received a 1-year contract through automatic renewal worth a total of $24,774. | | CL G. Roggenburk received a 1-year contract through automatic renewal worth a total of $24,774. | | SS T. Fuentes received a 1-year contract through automatic renewal worth a total of $24,774. | | MR J. Dickson received a 1-year contract through automatic renewal worth a total of $24,774. | | MR J. Warner received a 1-year contract through automatic renewal worth a total of $24,774. | | MR F. Burdette received a 1-year contract through automatic renewal worth a total of $24,774. | | Placed 1B E. Banks on the active roster. |
| Saturday, November 13th, 1965 | | CF L. Brock received a 1-year contract through arbitration worth a total of $406,800. | | SS R. Petrocelli received a 1-year contract through arbitration worth a total of $282,420. | | MR F. Linzy received a 1-year contract through arbitration worth a total of $158,336. | | SP G. Gerberman received a 1-year contract through arbitration worth a total of $296,028. | | 2B K. Hubbs received a 1-year contract through arbitration worth a total of $24,774. | | C D. Bertell received a 1-year contract through arbitration worth a total of $24,774. |
| Wednesday, November 3rd, 1965 | | Signed free agent 1B E. Banks to a 1-year contract worth a total of $40,000. |
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