In his first game for the "Toffees" he provided the crosses for Dixie Dean to score four goals in a 5–4 win against Sunderland. In his first full season at Goodison Park, 1927–28, Everton won the First Division league title. He provided many of the passes that enabled Dixie Dean's record-breaking 60 goals. However Everton dropped to 18th in 1928–29, before being relegated in last place in 1929–30. Everton then won the Second Division championship in 1930–31, and won the First Division title again in 1931–32. They dropped to 11th in 1932–33, and Critchley missed the FA Cup Final victory over Manchester City at Wembley after he had scored the winning goal in the semi-final victory over West Ham United, with Albert Geldard selected ahead of him for the final. The 1933–34 season was his last for Everton. In all, Critchley scored 42 goals in 230 games for Everton before being transferred to Preston North End in 1934.