Twelve months later Dundee became the first club to retain the League Cup when they defeated Kilmarnock 2-0 in the Final and with a Scottish Cup Final defeat to Motherwell squeezed in between the two League Cup wins, Anderson had finally turned Dundee in a trophy winning, Scottish footballing force.
While the early fifties brought cup glory, the rest of the decade would see dismay for the Dark Blues in the country's main competition notably with a three nil defeat in the season 1953/54 by C Division Berwick Rangers.
Things got worse five years later when in January 1959 Dundee visited to Highland League Fraserburgh in the Scottish Cup first round and crashed out with an embarrassing 1-0 loss. With a team that was full of experience and youthful promise, the Dark Blues had Bill Brown and Doug Cowie both of whom appeared for Scotland at the previous year's World Cup Finals, alongside Jimmy Gabriel who would go on to have a fine career with Everton, Hugh Robertson, Alan Cousin, Bobby Cox and Alex Hamilton. On paper Dundee should have been comfortable winners but the defeat to 'The Broch' is perhaps the biggest shock defeat ever from a Highland League Club.
However Robertson, Cousin, Cox and Hamilton didn’t have long to wait for honours, for in season 1961/62 the Dark Blues had their most glorious season, beating Rangers 5-1 at Ibrox and winning the Scottish League championship with a 3-0 win at Muirton Park, Perth on the final day of the season.
The names of Liney, Hamilton, Cox, Seith, Ure, Wishart, Smith, Penman, Cousin, Gilzean and Robertson trip off the tongue of every Dundee fan young and old and managed by Bob Shankly, they were described by Scottish Football historian Bob Crampsey as ‘the best Scottish footballing side to emerge in Scotland since the war, better even than the Lisbon Lions.’
Shankly brought together a blend of players both on and off the park who allowed Dundee to live their dreams. There were the young stars like goal scoring phenomenon Alan Gilzean, who had trained as a painter and decorator, Ian Ure, who had given up rugby to play football for Dundee and Andy Penman, the ‘Penalty King’, the homesick genius whom Willie Thornton had rescued from Everton at the tender age of fifteen.
There was the ageing genius Gordon Smith who had been put out to pasture by Hearts with four championship medals in his pocket, whom Bob Shankly picked up for nothing at the age of 37 and who would play in a European Cup semi-final at 39. There were fellow veterans Bobby Wishart and Bobby Seith who had championships behind them with Aberdeen and Burnley respectively and who would bring vital experience to a young team.
There was Alan Cousin, the part-time footballer who juggled his playing career with school teaching and whose double shuffle was something that could never be taught. There was Hugh Robertson, deft and electric on the left wing and Pat Liney, without whom the Championship might not have been won had he not saved a penalty against St.