The brilliant full back, who was equally at home on either side, made his debut in 1953 at the age of 19 in the company of players such as Woodburn, Sammy Cox and Waddell, and ended his Ibrox days in 1966 alongside Greig, Henderson and McKInnon.
He was a good tackler who would time his challenges well but his greatest gift was his speed.
Caldow always had enough pace to recover and get back at his man if beaten on the ground.
Born in Cumnock on May 14 1934, his association with Rangers began when he was 14.
He was sent to Muirkirk Juniors to develop his natural skills and returned to Ibrox aged 18.
The next season Caldow got his chance in a 4-2 League Cup win over Ayr in September 1953. He played eight League games that term, standing in for the great George Young.
By 1955-56, when Rangers won the championship, he had become a regular at right back.
But the following season, when the title was retained, Caldow began to play more at left back, forming a partnership with Bobby Shearer.
European football was still in its infancy when Caldow led Rangers into their first final – the Cup Winners Cup Final of 1961 – having disposed of Ferencvaros, Borussia Monchengladbach and Wolverhampton Wanderers, then one of the strongest teams in England, along the way.
The skipper, however, was unable to lift the trophy, losing out 4-1 on aggregate to Italian cracks Fiorentina.
Caldow won his second winners’ medals in both the Scottish Cup and the League Cup in 1961-62. Hearts were beaten 3-1 in a replayed League Cup final and St Mirren 2-0 in the Scottish FA Cup. His fifth and final Championship came in 1962-63.
Caldow played 40 times for Scotland – 29 at left back and 11 at right – and captained them for three years.
He won his first international cap in a 4-2 victory over Spain in May 1957 and the next year played in all three of Scotland’s games in the World Cup in Sweden.
However, his international career was ended in horrific circumstances at Wembley in 1963 – ironically the day when the man in front of him, Jim Baxter, secured vitctory for the Scots.
He broke his leg in three places after only six minutes of the game when tackled by the England centre forward Bobby Smith.
He had been an automatic choice for Scotland since his debut and had missed only two games for Scotland in six years.
It took Caldow a long time to recover and the following season he played only three league games. His place at left back was taken by David Provan.
By 1964-65 Caldow had fought back and re-established himself. Provan switched to right back and Caldow played 26 League games on the left.
In turn, Caldow got his third League Cup winners’ medal as Rangers beat Celtic 2-1 in the Final.
That was to be his swansong. Caldow was 32 and played only three games in his final season of 1965-66.