Street made his first-class debut for Derbyshire in the 1887 season in July against Lancashire when he ended the game at 15 not out. In his second match against Yorkshire he made 9.
Street's cricket career began with Derbyshire in the 1887 season, where he made his first-class debut by reaching 15 runs without getting out in a game against Lancashire. His second match was against Yorkshire, where he scored a relatively low 9 runs.