Chicago (N) Cubs
All Transactions | _Cubs.png) | | | | Monday, September 1st, 1969 | | Purchased the contract of CL T. Abernathy from Triple A Texas. |
| Sunday, August 17th, 1969 | | Signed LF T. Reynolds to a 2-year contract extension worth a total of $152,000. |
| Saturday, June 21st, 1969 | | Signed SP G. Hobbie to a 2-year contract extension worth a total of $140,000. | | Signed C J. Grote to a 2-year contract extension worth a total of $190,000. |
| Sunday, May 4th, 1969 | | Signed SP S. Blass to a 3-year contract extension worth a total of $867,000. |
| Saturday, May 3rd, 1969 | | Signed RF R. Snyder to a minor league contract extension. |
| Thursday, May 1st, 1969 | | Purchased the contract of LF T. Reynolds from Triple A Texas. |
| Sunday, April 20th, 1969 | | Signed free agent RF R. Snyder to a minor league contract. |
| Sunday, December 15th, 1968 | | Drafted MR V. Blue in the 1968 first-year player draft (Round 1, Pick 7, 7th overall Pick). | | Drafted CF B. Day in the 1968 first-year player draft (Round 2, Pick 9, 33rd overall Pick). | | Drafted MR P. Borbon in the 1968 first-year player draft (Round 2, Pick 11, 35th overall Pick). | | Drafted SP S. Renko in the 1968 first-year player draft (Round 3, Pick 7, 55th overall Pick). | | Drafted CF R. Woods in the 1968 first-year player draft (Round 4, Pick 7, 79th overall Pick). | | Drafted MR P. Doyle in the 1968 first-year player draft (Round 5, Pick 7, 103rd overall Pick). |
| Wednesday, December 11th, 1968 | | Signed free agent CL S. Hamilton to a 3-year contract worth a total of $893,600. |
| Sunday, December 1st, 1968 | | Placed MR J. Cullen on the 40-man roster. |
| Thursday, November 28th, 1968 | | Signed RF D. Murphy to a minor league contract extension. | | Signed SP J. Owens to a minor league contract extension. | | Signed SS D. Robertson to a minor league contract extension. | | Signed MR M. Steevens to a minor league contract extension. |
| Tuesday, November 26th, 1968 | | Signed SP C. Estrada to a minor league contract extension. |
| Monday, November 25th, 1968 | | Signed RF J. McAnany to a minor league contract extension. | | Signed 1B M. Morhardt to a minor league contract extension. | | Signed C M. Thacker to a minor league contract extension. |
| Sunday, November 24th, 1968 | | Signed CL T. Abernathy to a minor league contract extension. |
| Monday, November 11th, 1968 | | MR E. Watt received a 1-year contract through automatic renewal worth a total of $29,439. | | SP B. Odom received a 1-year contract through automatic renewal worth a total of $29,439. | | RF B. Robinson received a 1-year contract through automatic renewal worth a total of $29,439. | | 2B S. Huntz received a 1-year contract through automatic renewal worth a total of $29,439. | | SP G. Gerberman becomes a free-agent. | | 3B D. Rader received a 1-year contract through automatic renewal worth a total of $29,439. | | C R. Fosse received a 1-year contract through automatic renewal worth a total of $29,439. | | SP D. Chance becomes a free-agent. |
| Friday, November 8th, 1968 | | C J. Grote received a 1-year contract through arbitration worth a total of $94,679. | | RF B. Ott received a 1-year contract through arbitration worth a total of $29,439. | | MR J. Warner received a 1-year contract through arbitration worth a total of $39,168. | | SS T. Fuentes received a 1-year contract through arbitration worth a total of $29,439. | | LF T. Reynolds received a 1-year contract through arbitration worth a total of $29,439. | | SP F. Jenkins received a 1-year contract through arbitration worth a total of $369,792. | | SP S. Blass received a 1-year contract through arbitration worth a total of $202,729. | | 1B W. Parker received a 1-year contract through arbitration worth a total of $29,439. | | MR J. Curtis received a 1-year contract through arbitration worth a total of $29,439. | | MR F. Burdette received a 1-year contract through arbitration worth a total of $103,003. | | 2B D. Johnson received a 1-year contract through arbitration worth a total of $49,266. |
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