West Bromwich born inside right Charlie “Chippy” Simmons began his football career with Trinity Victoria in 1895 and played for Olbury Town in 1896 and Worcester Rovers (which not long thereafter became Worcester City) in 1897, before joining First Division club West Bromwich Albion. He made his Football League debut at Burnley in November 1898, and whilst failing to score in his debut season, he notched 15 goals in 1899-1900, appearing regularly for the first team. When West Bromwich were relegated the following season, he stayed at the club and top scored with 24 goals during the campaign as Albion re-gained their top flight status at the first attempt winning the Second Division Championship in 1902. His haul included a hat-trick against Blackpool in February 1902.
However Albion were again relegated two seasons later, and this time Simmons left The Hawthorns, moving to Southern League club West Ham United for £700 in the summer of 1904 after 62 goals in 155 appearances for The Baggies. However he failed to settle in London, scoring 8 times in 35 appearances for The Hammers before returning to West Bromwich Albion for £600 10 months later. After 16 goals in his first season back at The Hawthorns, he lost his place in 1906, and joined Chesterfield Town in the 1907 close season after a further 19 goals in 38 appearances for The Baggies. He scored 8 times in 35 appearances during his single season at Saltergate, before leaving The Spireites for non league Wellington Town in 1908. He then left England for Canada in 1909, playing there for Royal Rovers.