Prior to his minor league and Major League career, Olivo spent many years playing in his native Dominican Republic. Diomedes Olivo posted a 55–29 win–loss record in the Double-A Mexican League from 1955–1959, then made his Major League debut with the Pirates at age 41 on September 5, 1960. His age at the time of his MLB debut is the oldest with the exception of Satchel Paige in the post-World War II era. In his first game, he pitched two scoreless innings of relief against the Milwaukee Braves, allowing one hit (to eventual Hall of Famer Eddie Mathews) and two bases on balls.\n', '

Olivo\'s best MLB season came in 1962. At age 43, he worked in 62 games, all but one in relief, and posted a 5–1 record and 2.77 earned run average in 84⅓ innings pitched, with seven saves. He then was included, with shortstop Dick Groat, in a major off-season trade to the Cardinals, but while Groat sparkled in St. Louis, Olivo lost all five decisions and spent part of 1963 in the minor leagues. He retired at age 44 following that season.\n', '

During his MLB career, Olivo allowed 112 hits and 39 bases on balls in 107⅓ innings pitched, striking out 85.\n', '

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