 Rangers retained the League title the following season, 1956–57, and Caldow was once again an important member of the team, making 40 appearances, this time mostly at left-back.Caldow continued to be an integral member of the Rangers team, featuring 49 times in 1957–58, including four European Cup matches against AS Saint-Étienne and AC Milan.Caldow also played in all of Scotland's three World Cup matches against Yugoslavia, Paraguay and France.