Reportedly rejected by Clyde due to his fierce temper, he moved south of the border to join Liverpool in 1899, and figured for Liverpool in their first four games of the 1899–1900 season, but lost his place to John Walker and only played one more match that season.
Unhappy with reserve-team football, he left in summer 1900 and went on to play for a range of Southern League clubs, including Leicester City (1900–01), West Ham United (1901–02), Kettering Town (1902–05) and Tottenham Hotspur (1905–06).
At Tottenham, he was reportedly involved in a fracas with teammate Christopher Carrick and suspended by the club.
The following season, Kyle was the Reds' top scorer with nine goals (eight in the league and one in the FA Cup), although Arsenal's form was much poorer and they only finished 14th.
[3] Kyle was not as big a success at Villa as he had been with Arsenal, and after less than a year he had moved on to Sheffield United, (with Robert Evans for a combined fee of £1100).