The lanky 6 ft 2 ½ inch 190 pound Bob Chipman broke into the majors in his hometown of Brooklyn with the Dodgers in 1941, but pitched mostly in the minors until traded to the Chicago Cubs on June 6 1944 for infielder and future major league manager Eddie Stanky.
Bob Chipman sparkled right-off-the-bat with the Chicago Cubs, and finished his first year in the Windy City with a 12-10 record, with a 3.65 ERA in 37 games, completed 9 of 24 starts. In 1945 he split his pitching duties with starting and relieving roles and helped the Cubs win the pennant. In the World Series Bob Chipman relieved in one game, working 1/3 innings, no-hits allowed. The Cubs ace relieved or started in 38 games in '49 and had the second best ERA on the Cubs staff - 3.98... he flashed excellent form the last part of the season... in 1949 Bob Chipman was 7-8 in 113 innings.
Bob Chipman pitched the last three seasons with the Boston Braves as a starter and reliever.