The first event was held in 1903 at the Myopia Hunt Club and won by Arther Lockwood. Thirty-eight contestants entered from the 42 MGA member clubs. The most famous winner of the championship was six-time champion Francis Ouimet. Other notable winners include Jesse Guilford, Dick Chapman and Eddie Lowery. Fred Wright holds the record with seven titles (1920, 1926, 1927, 1928, 1929, 1931, and 1938).

Since 1992, five Massachusetts Amateur Champions have turned professional: Trevor Gliwski, Flynt Lincoln, James Driscoll, Jim Salinetti and Rob Oppenheim. 2008 marked the 100th playing of the Massachusetts Amateur. Today the tournament holds a field of 144 players from 400 golf facilities across the state. The Championship starts with two days of stroke play. The low 32 scores continue on to match play competition.

• Massachusetts Golf Association
• List of winners