Kettering, Northamptonshire born outside right Herbert Winterhalder began his football career with hometown Southern League club Kettering in 1900, his first senior level match being an FA Cup 1st round tie against Crewe Alexandra in January 1901 which Kettering won 1-0. From there joined First Division Sheffield United in 1902, making his Football League debut at Middlesbrough the same November as he played in a cluster of 6 games in November and early December, scoring in two of them.
He played in 5 more games for The Blades before the season’s end but moved to Plymouth Argyle in the summer of 1903 as the club turned professional. He played regularly during Argyle’s first campaign, scoring 7 goals in 33 appearances before moving on at the end of their inaugural season to join Southern League Wellingborough in the 1904 close season. After a season in Northamptonshire he moved to West Ham United and made his debut against Luton Town in September 1905, making 4 appearances for The Irons in September and early October. However he never got back into their first team and re-joined Kettering in 1907 where he finished his career.
NB despite the highly unusual surname and the fact that they played together at West Ham United, he is not thought to have been related to Arthur Winterhalder.