Billy Holland was one of the top black pitchers of the late 1890s and early 1900s, but pitched at a time when Organized Baseball was either entirely or almost entirely segregated and the Negro Leagues had not yet been formed. Top black teams almost never played each other, leading to almost no official statistical track record by which we can judge Holland. He joined the Chicago Union Giants in 1894, then spent either two or part of three years with the Page Fence Giants. He pitched part of a game against the Cincinnati Reds in 1895. He returned to the Union Giants in 1897 and pitched in a 5-5 tie against the Indianapolis Indians in 1899. He was with the Algona Brownies in 1903, the Leland Giants in 1905. Known for his humorous antics on the field, Holland's career ended after spending the 1907-08 seasons with a lesser black team. In the 1920s he was an umpire in the Negro National League.