Holloway was born in Barwick, Georgia, in 1897. He attended the University of Georgia. In May 1918, he was picked by the Auburn baseball coach in The Atlanta Constitution as a pitcher on the all-star nine of college baseball. Listed at 6 ft 0 in (1.83 m), 185 lb., Holloway batted and threw right-handed.\n', '

A curveball specialist, Holloway entered the majors in 1922 with the Detroit Tigers, remaining with the club for seven years from 1922 to 1928. He appeared in 237 games for the Tigers, 97 of them as a starter and the rest as a relief pitcher. He compiled 57–46 win–loss record and a 4.41 earned run average (ERA) with the Tigers. His best seasons were 1924 and 1925 when he compiled a combined 27–10 record with a 4.33 ERA. His .700 winning percentage in 1924 was second only to Walter Johnson, and his .765 winning percentage in 1924 was second only to Stan Coveleski. His nine relief victories led the American League in 1924.\n', '

In December 1928, Holloway and Jackie Tavener were traded to the Cleveland Indians in exchange for pitcher George Uhle. Holloway appeared in 25 games for the 1928 Indians, 11 as a starter, and compiled a 6–5 record with a career low 3.03 ERA. In 1930, he began the season with Cleveland, appearing in 28 games and compiling a 1–1 record with a career high 8.40 ERA.\n', '

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