Bailey was born in
Streatham and was educated at
Westminster School, whom he represented at football. He subsequently played for the
Old Westminsters,
Clapham Rovers,
Wanderers,
Swifts and
Corinthian, as well as earning representative honours for
Surrey and London. At his peak he was described as "a very safe half-back, with plenty of dash and judgement; he has both strength and pace and never misses his kick". He was a member of the
Clapham Rovers team that reached the
FA Cup final twice, losing 1-0 to
Old Etonians in
1879, and going on to win the cup in
1880 with a 1–0 win over
Oxford University at
The Kennington Oval. He made 19 appearances (scoring once) for the
England national football team between 1878 and 1887 (and was thus the first player to make more than ten appearances for his country) and
captained England fifteen times. ==After football==