Triumph Motorcycle News Classic Motocross Iron: 1966 Matchless 500 G85CS April 17, 2018 Christopher Bradley Leave a comment The first Matchless single-cylinder motorcycle rolled off the assembly line in 1901. In 1905 Matchless began manufacturing motorcycles using J.A. Prestwich V-twin engines, and by 1912 the company was producing its first complete in-house machine.