Season 1948/49 saw Dundee reach the semi-finals of both the League and Scottish Cups and in the League Championship finished second after a heart breaking last day defeat. Dundee were one point ahead going into the final match at Falkirk and a win would guarantee the League Flag, regardless of what Rangers did at Albion Rovers but it wasn’t to be.
The Dundee players were flooded with nerves and the effervescent and chirpy Anderson was unable to dispel them. When confronted with the usual pre-match opposition banter, Anderson locked his troops in the dressing room an hour before kick off and tried to protect his players from unnecessary distractions. It back fired however as Dundee first missed a penalty while at 0-0 and then fell apart in the second half and went down 4-1 as Rangers snatched the title with a similar score line at Coatbridge.
In just five short years however, Anderson had taken Dundee from Division Two also-rans to Championship contenders but the fact was, that there was no major trophies in the Dens Park cabinet and he had to work out how he was going to change that.
However it was the signing George Anderson made in September 1950 which was the final piece in the jigsaw, when pulled off one of the transfer coups of the century when he signed Scottish superstar Billy Steel for a world record fee of £23, 500. Anderson had fought off competition from Rangers to land Steel and the inside forward brought power, skill and imagination to the Dundee forward line. It was extraordinary for a provincial club like Dundee to pay such an extraordinary fee and Anderson’s philosophy of ‘think big’ was repaid when silverware was soon on its way to Dens.
With the strong back-line of Cowie, Gallacher and Boyd added to the goals of Flavell and the skill of Steel, Dundee won their first trophy since 1910 when on October 27th 1951, Dundee won the League Cup in an exciting 3-2 win over Rangers at Hampden.