Holland was the mainstay of the New York Black Yankees' pitching staff in the 1930s. Of his 22 years in baseball, 18 were spent in New York. He was the first black pitcher to pitch in Yankee Stadium when he beat the Baltimore Elite Giants before a crowd of 15,000 in 1930.
The 5'8" 175-lb Holland joined his first pro team, the Detroit Stars, in 1920. In 1922 he led the league with 16 wins. Hall of Famer Cool Papa Bell ranked Holland with Satchel Paige, Smokey Joe Williams, and Bullet Joe Rogan as the best pitchers in the Negro Leagues. Though he relied mainly on the fastball, he also expertly mixed in a curve, a drop, a changeup, and an occasional emery ball.