Rangers regained the Scottish Cup in 1966 against Celtic but lost out in the other competitions to the same opponents, who were beginning a period of dominance. Wilson played in both cup finals but made only 21 appearances overall, his fewest since 1958. Wilson's last campaign with Rangers was 1966–67, as Willie Johnston and new signing Alex Smith became the preferred choice's on the left flank. He made 29 appearances and scored 8 goals, being introduced as a substitute for Johnston in the League Cup final loss to Celtic and the infamous Scottish Cup defeat to Berwick. He did not feature in Rangers' second Cup Winners' Cup Final although he played his part in the run including the winning goal in the semi-final, away to Slavia Sofia.