Played for a local side Ashton North End before moving on to Stalybridge Rovers and Rochdale.
Made his league debut after signing for Grimsby in 1898.
He moved around, taking his career through Swindon Town, Sheppey United, Worksop and Northampton Town. Then Herbert moved to Sheffield United, Notts County and finally back to Northampton Town.
Arrived at White Hart Lane for £75 from the Cobblers in March 1905.
Started as a manager at Northampton Town and later moved on to take control at Leeds City, Huddersfield Town and Arsenal.
Lodged in Trulock Road (at the rear school at the back of the ground) during his Spurs playing days.
Scored 16 goals in 42 games in the Southern League for Tottenham.