Jackson played for Cambridge University, Yorkshire and England. He spotted the talent of Ranjitsinhji when the latter, owing to his unorthodox batting and his race, was struggling to find a place for himself in the university side, and as captain was responsible for Ranji's inclusion in the Cambridge First XI and the awarding of his Blue. According to Alan Gibson this was "a much more controversial thing to do than would seem possible to us now". He was named a Wisden Cricketer of the Year in 1894.