| | | Tuesday, May 6th, 1969 | | Signed MR Paco Román to a 2-year contract extension worth a total of $12,780,000. |
| Friday, April 11th, 1969 | | Signed 2B Enrique Fabián to a 2-year contract extension worth a total of $25,000,000. |
| Saturday, February 15th, 1969 | | Signed free agent SP Derrick Tiedeman to a 1-year contract worth a total of $13,700,000. | | Signed free agent 1B Jeff Austin to a 1-year contract worth a total of $10,770,000. |
| Saturday, January 25th, 1969 | | Signed free agent 1B Mark Courtemanche to a 1-year contract worth a total of $490,000. |
| Monday, January 20th, 1969 | | Signed free agent RF James Anderson to a 1-year contract worth a total of $450,000. | | Placed RF James Anderson on the active roster. |
| Sunday, November 24th, 1968 | | SP E. Wardrope received a 1-year contract through automatic renewal worth a total of $300,000. | | 2B C. Ross received a 1-year contract through automatic renewal worth a total of $300,000. | | 1B H. Benson received a 1-year contract through automatic renewal worth a total of $300,000. | | 1B G. Rodríguez received a 1-year contract through automatic renewal worth a total of $300,000. | | LF B. O'Quinn received a 1-year contract through automatic renewal worth a total of $300,000. | | RF J. Fabela becomes a free-agent. | | LF N. McLewis received a 1-year contract through automatic renewal worth a total of $300,000. | | SP S. Maldonado received a 1-year contract through automatic renewal worth a total of $300,000. | | 1B K. Schroeder received a 1-year contract through automatic renewal worth a total of $300,000. | | SS J. Aguilera received a 1-year contract through automatic renewal worth a total of $300,000. | | C C. Miller received a 1-year contract through automatic renewal worth a total of $300,000. | | 2B M. Britton received a 1-year contract through automatic renewal worth a total of $300,000. | | RF J. Jones received a 1-year contract through automatic renewal worth a total of $300,000. |
| Thursday, November 21st, 1968 | | LF J. Schneider received a 1-year contract through arbitration worth a total of $300,000. | | 3B J. Contreras received a 1-year contract through arbitration worth a total of $5,882,800. | | SP F. Villarreal received a 1-year contract through arbitration worth a total of $6,016,000. | | CL F. Rosales received a 1-year contract through arbitration worth a total of $3,105,000. | | SS O. Toyota received a 1-year contract through arbitration worth a total of $6,230,800. | | 2B E. Fabián received a 1-year contract through arbitration worth a total of $6,800,000. | | SS P. Charon received a 1-year contract through arbitration worth a total of $300,000. | | 1B S. Flake received a 1-year contract through arbitration worth a total of $300,000. | | MR T. Kennedy received a 1-year contract through arbitration worth a total of $3,070,500. | | RF M. Vázquez received a 1-year contract through arbitration worth a total of $300,000. |
| Friday, November 1st, 1968 | | SP A. Deel retires. |
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