Boston Red Sox
Major Transactions |  | | | | Tuesday, September 16th, 1969 | | Placed 1B A. Shamsky on the active roster. | | Activated 1B A. Shamsky from the disabled list. |
| Friday, August 1st, 1969 | | Placed SP B. Friend on the active roster. |
| Thursday, July 17th, 1969 | | Signed free agent SP B. Friend to a 1-year contract worth a total of $53,400. |
| Saturday, May 17th, 1969 | | Signed MR B. Priddy to a 3-year contract extension worth a total of $359,400. |
| Friday, May 16th, 1969 | | Traded 22-year old minor league starting pitcher G. Gentry to the Chicago (N) Cubs, getting 21-year old minor league catcher C. Fisk in return. |
| Sunday, May 4th, 1969 | | Signed MR W. Schurr to a 3-year contract extension worth a total of $1,637,000. |
| Wednesday, January 22nd, 1969 | | Placed SP B. Bolin on the active roster. |
| Wednesday, January 15th, 1969 | | Signed free agent SP B. Bolin to a 4-year contract worth a total of $5,532,000. |
| Monday, December 16th, 1968 | | Placed SS A. Rodgers on the active roster. |
| Saturday, December 14th, 1968 | | Signed free agent SS A. Rodgers to a 2-year contract worth a total of $116,800. |
| Monday, December 2nd, 1968 | | Signed SP W. Wood to a 7-year contract extension worth a total of $7,250,600. |
| Sunday, December 1st, 1968 | | Drafted LF A. Johnson in the 1968 rule 5 draft (Pick 19, Round 1, 19th overall Pick). | | Drafted 2B B. Saverine in the 1968 rule 5 draft (Pick 19, Round 2, 43rd overall Pick). |
| Monday, November 11th, 1968 | | SS E. Bressoud becomes a free-agent. | | C M. Sanguillen received a 1-year contract through automatic renewal worth a total of $29,439. | | CF D. Unser received a 1-year contract through automatic renewal worth a total of $29,439. | | 1B M. Fiore received a 1-year contract through automatic renewal worth a total of $29,439. | | SP J. Nash received a 1-year contract through automatic renewal worth a total of $29,439. | | C E. Hendricks received a 1-year contract through automatic renewal worth a total of $29,439. | | MR D. Lines received a 1-year contract through automatic renewal worth a total of $29,439. | | MR J. Verbanic received a 1-year contract through automatic renewal worth a total of $29,439. |
| Friday, November 8th, 1968 | | MR L. Foster received a 1-year contract through arbitration worth a total of $199,152. | | MR B. Priddy received a 1-year contract through arbitration worth a total of $77,810. | | MR W. Schurr received a 1-year contract through arbitration worth a total of $368,480. | | SS H. Clarke received a 1-year contract through arbitration worth a total of $561,556. | | 2B J. Donaldson received a 1-year contract through arbitration worth a total of $360,828. | | LF A. Shamsky received a 1-year contract through arbitration worth a total of $364,392. | | SP S. Hargan received a 1-year contract through arbitration worth a total of $536,142. | | SP D. Boswell received a 1-year contract through arbitration worth a total of $290,176. |
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