Bob Gillespie was born on October 8, 1919, in Columbus, Ohio. He played American Legion and sandlot ball, winning athletic honors in track and basketball, as well as baseball. He hadnít really intended to go into baseball in particular, but after he graduated from South High School in Columbus, he was playing baseball in a Saturday afternoon league, making a little extra money.

He caught the eye of a Detroit Tigers scout, who offered him a minor-league contract at $175 a month. His first year in professional baseball was in 1940, and he did indeed pitch in two games at Beaumont, for a total of one inning. Most of the year however, was spent in the Class-C East Texas League pitching for the Henderson Oilers. 

In 1941 he pitched three innings for Beaumont and most of his year was in the Class-B Piedmont League, pitching for the Winston-Salem Twins. In 1942, Bob pitched for Beaumont all season long. He didnít play organized ball in 1943, but neither did he serve in the armed services. Heíd been rejected by the Army, but spent the year working in a defense plant, an arms factory.

Near the end of March 1944, things changed and he reported to the Tigers and made his debut at Yankee Stadium. In June he was optioned to Buffalo. He did join the Tigers for spring training, albeit late, and pitched for Buffalo again in 1945.  In 1946 he spent another year in the minors, this time for the Double-A Dallas Rebels of the Texas League. 

In November, the Chicago White Sox selected him from the Tigers in the Rule 5 draft and the White Sox took him to the majors for two years running, 1947 and 1948. By the time it was all over, he was 5-8 with a 4.73 ERA. During the offseason, he had hernia surgery, then suffered a relapse during spring training in 1949.

In October, the White Sox released him outright to Memphis and in December, the Memphis Chicks sold his contract to the Sacramento Solons of the Pacific Coast League, where had a very good year. In October, Sacramento club officials announced his sale to the Boston Red Sox. 

Bob joined the Red Sox at Sarasota for spring training. He was pleased at the prospect of making the team because the Red Sox were stacked with sluggers, but lacking pitching and he was one of 15 pitchers manager Joe McCarthy was looking over. Bob made the team out of spring training, but the realization of the dream lasted for 10 batters in 1 1/3 innings. 

In May, the Sox returned him to Sacramento. He devoted two more years to the pursuit of baseball, again with Sacramento in 1951 and a final season in the Carolina League with Reidsville.

After baseball, Bob worked as the foreman in the newspaper pressroom of Piedmont Publishing of Winston-Salem, North Carolina.

Bob Gillespie passed away at age 82, on November 4, 2001, in Winston-Salem, North Carolina.