attended Brookland-Cayce High School in Cayce, South Carolina. He played in the PONY League as a youth, appearing in regional league finals in 1954. He never attended college. His brothers, Alfred Womack and Larry Womack, were minor league pitchers who never reached the major leagues. Alfred, also known as "Al", pitched in the Cleveland Indians and Washington Senators systems in 1955 and 1956. Larry pitched in the Yankees' system in 1968. Womack, who acquired his nickname "Dooley" as a child from a friend of his family and claimed, "I prefer it to my real name, which is Horace," was described as having a "high voice, a serious drawl and a giddy laugh", by Maury Allen in his book Where Have You Gone?. He was also described as a fan favorite, attributable to his smile and style. Professional career Before the major leagues Womack spent eight seasons in the minor leagues before making his major league debut. 1958–1959 On June 25, 1958, Yankees scout Ted Petoskey signed the 18-year-old Womack to a contract, giving him a $2,500 bonus. He reported to the St. Petersburg Saints of the Class-D Florida State League the following day and on July 5, he made his first professional appearance, a start against the Cocoa Indians. In his first game, he allowed eight hits, four walks and three earned runs in seven innings, while striking out six batters, earning the victory. Offensively, he collected one hit in four at-bats and scored a run. Womack pitched in 11 games for the Saints that season, making eight starts and going 6–3 with a 2.38 ERA, allowing 52 hits in 68 innings of work. He was the only pitcher on the 1958 Saints to ever make the major leagues. At the plate, he hit .276 with 4 RBI, collecting eight hits in 29 at-bats. Prior to the start of the season, it was believed that Womack would begin 1959 with the St. Petersburg Saints, however he was released and sent to the Fargo-Moorhead Twins of the Class-C Northern League. He spent his entire season with the Twins, going 13–9 with a 4.50 ERA in 31 games (22 starts). In 172 innings, he allowed 175 hits, 18 home runs and 86 earned runs to score. He led the team in losses and home runs allowed and finished second in victories, games, games started, innings pitched, hits allowed, runs and earned runs