 In April 1906 he joined Woolwich Arsenal and made his debut on the first day of the 1906-07, in Arsenal's First Division win over Manchester City on 1 September 1906.That season, he was prolific in front of goal, scoring thirteen goals in 29 league appearances (although Charlie Satterthwaite was Arsenal's top scorer that season) as Arsenal finished seventh.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.