He moved to Everton in 1927 for £7,000, at the age of 30, where he played alongside goal machine Dixie Dean. He won the league title in 1927–28, his first season at Goodison Park. They then won the subsequent Charity Shield in 1928, before finishing a disappointing 18th in 1928–29, just three places above the drop. Everton then finished bottom of the division in 1929–30, though were just one point behind third-from-bottom (and therefore not relegated) Sheffield United. The "Toffees" made an immediate return to the top-flight, marching to the Second Division title in 1930–31, seven points ahead of runners-up West Bromwich Albion; they scored 121 goals in their 42 league games. They continued their success into the First Division, winning the title in 1931–32 after finishing two points ahead of Arsenal. Their success continued in the Charity Shield in 1932, as they beat Newcastle United 5–3 at St James' Park. They dropped to eleventh in 1932–33, but lifted the FA Cup in 1933. The final, held in front of 92,950 spectators at Wembley, finished in a 3–0 victory over Manchester City, and the "Manchester Guardian" described Cresswell as giving "an almost perfect display". The club's final two seasons under manager-secretary Thomas H. McIntosh ended with a whimper however, with a 14th-place finish in 1933–34 and an eighth-place finish in 1934–35. Theo Kelly led Everton to a 16th-place finish in 1935–36, Cresswell's last as a professional footballer. Retiring at the age of 38 having made 306 appearances for the club, after his death he was inaugurated into the Gwladys Street's Hall of Fame.