After attending both Georgia Tech and Middle Tennessee State, Bob Tillman signed with the Red Sox in 1958. Two years later, he caught for the Triple-A, Minneapolis Millers, a team that included future major league teammates Carl Yastrzemski, Dick Radatz, and Earl Wilson.

With the Seattle Rainiers, Bob played for manager Johnny Pesky in 1961, with whom he would be reunited in 1963 when Pesky took over as manager for the Red Sox. Pesky was impressed with his power numbers.

In 1962, Bob stuck with the big club out of spring training. But with two other catchers, Russ Nixon and Jim Pagliaroni, on the roster, he appeared in just over half of the games. He ended the year with 14 home runs but batted only .229.

The 1963 season saw increased action for him. Unfortunately, despite his high hopes it was not a good year at the plate, where he continued to struggle, hitting .225. Pesky did not lose faith in him, however, installing him as the starter in 1964, and he responded with what would turn out to be his best year offensively, hitting .278 with 17 home runs.

Bob's playing time dropped in 1965, and in 1966, he played in 78 games as Mike Ryan’s backup, hitting .230 with three homers.

And then came 1967, which saw former teammate Dick Williams take the helm in the spring. Unfortunately, in a game against the Tigers, while trying to cut down Al Kaline stealing second, his throw was interrupted by relief pitcher John Wyatt’s head. After that, he became the prime tenant of Williams’ doghouse.

After acquiring Elston Howard, the Red Sox had four catchers and someone had to go, so Bob was sold to the Yankees in August.

Bob Tillman passed away at age 63, on June 23, 2000, in Gallatin, Tennessee.