Billy began playing baseball on a team in Aurora, IL named Pug's Colts.

[6] Holland made his professional debut at the age of 20 with the Chicago Unions in 1894, and moved to the Page Fence Giants in 1895.

Holland pitched for the Algona Brownies, and in September 1903 was involved in an incident in St. Paul, Minnesota where one of his pitches went wild and hit Winnipeg player William W. Kelley on the head, fracturing his skull.

Holland was arrested by local police, after leaving the game and traveling to the city on a street car.

The two teams were set to tour together throughout Minnesota, playing each other at county fairs.