 After finishing third that season, Rangers regained the League title in 1958–59, with Caldow missing just one match.Caldow won his first Scottish Cup medal in 1959–60, and despite failing to retain their League title, Rangers reached the semi-final of the European Cup, defeating Anderlecht, Cervena Hviezda Bratislava and Sparta Rotterdam before eventually losing to German club Eintracht Frankfurt.European success continued for Rangers the following season as Caldow captained Rangers to the inaugural Cup Winners Cup final, defeating Ferencváros, Borussia Mönchengladbach and Wolverhampton Wanderers before losing 4–1 to Fiorentina in the final.