Windley was one of South Melbourne's veteran players when they started out in the VFL, having played in the VFA since 1886, and been a regular selection since 1888.

An elusive player, he was a centreman in the VFA, but was often used as a rover later on in his career and also spent some time up forward.

In the VFL, he captained South Melbourne in 1900 and 1902, and also played in their losing 1899 Grand Final team.

Windley retired after Round 16 of 1905, one week after his 37th birthday, and was later a trainer and equipment manager at South Melbourne; his career total of 265 games remained the club record until it was broken by Michael O'Loughlin in Round 19 of 2007, 102 years after Windley's last match, 54 years after his death, and 26 years after the Swans' relocation to Sydney.

This Australian rules football biography of a person born in the 1860s is a stub.