Kay's career as Liverpool manager started poorly, with only three wins and four draws from the first twelve matches. This run included a 2–6 defeat at Portsmouth's Fratton Park on 2 September and a 2–5 defeat at Brentford; the only bright spot in this spell was a 7–1 victory over Grimsby Town on 12 September, with two goals from Fred Howe. Results improved slightly as the season progressed and Liverpool finished Kay's first season in charge in 18th place in Division 1.