The centre-half had two spells at Fosse around the turn of the century and made over 50 appearances for the Foxes during those two stints. He made his debut in September 1899 at Luton Town but spent less than a year at the club in his first spell.

A move to New Brighton Tower followed but Dainty soon returned to Filbert Street for a second spell as a Fox. Moves to Northampton Town, Notts County and Southampton followed but his reputation got a big boost thanks to his performances north of the border - with Dundee, where he spent six years as a player. He twice helped them to a runners-up spot and lifted the Scottish Cup in 1910.

He became somewhat of a Dundee legend and even returned there as a player-manager during World War 1. His career took a twist when he became the first British manager in Guayaquil, Ecuador for the new Barcelona club. He returned home to manage Kettering and be a trainer at Ipswich Town.