As the Blues prepare to begin our FA Cup campaign this weekend, we look back at a classic third-round tie against Liverpool, when Tommy Docherty’s Diamonds, led by two club legends in the making, upset the odds at Anfield.

In the mid-Sixties, it was one of English football’s long-running jokes: Chelsea’s failure to lift a trophy that was, at the time, viewed as the biggest of the lot in this country, the FA Cup.

We had won the league title in 1955 and 10 years later, under the bright, innovative leadership of one of the game’s youngest managers, Tommy Docherty, we had secured the League Cup. But still the big one eluded us and for a proud man like the Doc, who passed away late last year, it was clear he wanted to put a stop to this joke with a punchline of his own.

The Blues had gone close in 1965, losing out in the semi-finals to eventual winners Liverpool in a game that left a bitter taste, after we had what looked to be a perfectly good goal by centre-half John Mortimore chalked off by the referee for an apparent infraction.

You can imagine that lesser men would have shrunk at the news the two sides would meet again at Anfield – where we had not won since the 1935/36 season – in the third round of the following season’s competition, as Liverpool’s champions elect were drawn against the young upstarts.

As Bobby Tambling, Chelsea’s goalscorer extraordinaire, put it in his autobiography, Goals in Life: ‘The day you don’t want to play in a game like this is the day when you ought to be hanging up your boots.’

While there was little focus on it at the time, one can only imagine what today’s press would have made of the managers facing off against each other, two very quotable Scotsmen.

There was the older Shankly, looking to return Liverpool to the ‘perch’ that Sir Alex Ferguson infamously wanted to knock them off more than three decades later.

Then, his opposite number Docherty, not yet 40 but carving out a big reputation for himself as one of brightest minds in the business, leading a young side towards the summit of English football. For more on that, Blues fan Tim Rolls – who wrote a book about Docherty – provides plenty of colour in his tribute to the Doc.

Ahead of this tie against Liverpool, the latest Diamond to emerge was Peter Osgood, who was being tipped for a place in England’s World Cup squad after he had capped a virtuoso display against Tottenham Hotspur with the winning goal a week before our trip to the North-West.

Ossie had been told by Docherty a few months earlier that he was coming into the team ahead of Barry Bridges, who had just won his fourth, and ultimately last, England cap. What's more, the Doc assured him he would be given a run of games, regardless of how many goals he scored or how he performed, to become accustomed to the senior football. It was a bold move that would pay off in a big way – including in the thrilling tie at Anfield, when the youngster outlined his credentials against what was then the best team in the country.

Liverpool had gone ahead after only 90 seconds through Roger Hunt – who, unlike Osgood, did make the England squad and appeared in the victory over West Germany in the final – and at that point, Shankly admitted: ‘I thought we were going to tear them to pieces.’

‘However,’ continued the Reds boss, ‘we were a wee bit careless.’

Only five minutes later, Osgood stooped to head in our equaliser and he was relishing the opportunity to strut his stuff against top opposition. At one stage he picked up the ball inside his own half and embarked on a dribble that took him to the edge of the Liverpool box, prompting BBC commentator Kenneth Wolstenholme to exclaim: ‘This boy Osgood – he really is good!’

The Blues got in behind what Daily Mirror reporter Ken Jones described as Liverpool’s ‘strangely indecisive defence’ time and time again, although our misfortune from the previous year’s semi-final was perhaps repaid in kind when John Boyle got away with a blatant shirt tug in the box.

Finally, the game’s decisive moment arrived, with 66 minutes on the clock, and it was provided by a man who would later that year go on to become the club’s all-time leading scorer. Of course, it was Tambling, whose record stood for almost half a century before being surpassed by Frank Lampard.

‘I came in off the left wing to receive the pass from Venner and I laid the ball on to George Graham down the right,’ wrote Tambling in his book, having selected it at No.5 in a list of his favourite goals. ‘I carried on my run and George sent in a tremendous cross which I got my head to. It wasn’t a bullet header by any stretch. In fact, it looped over the defender and dropped just under the bar. What a result!’

The Blues held on, aided by some stunning saves by Peter Bonetti, to secure a famous victory at Anfield. Little did we know it would be another 26 years before the supporters would experience that feeling again.

With their hopes of retaining the FA Cup in tatters, Shankly could have been forgiven for not being magnanimous in defeat. However, the legendary Reds boss went completely the other way, saying, ‘That’s one of the greatest games you’ll ever see. Fantastic entertainment.’

Docherty’s Chelsea were elated to have come out on the right side of such a classic contest, with Tambling adding: ‘I’ll never forget the feeling in the dressing room after the game. It was absolutely wonderful and that carried on all the way back to London on the train.’

After seeing off the holders, the Blues were then, rather uniquely, drawn against the other finalist from the previous season: Leeds United.

This was the first of six cup encounters between the sides over five years, and a crowd just shy of 60,000 at the Bridge saw a feisty game settled 1-0 in the Blues’ favour by that man Tambling once again. It was the beginning of one of English football’s fiercest rivalries – but that’s a story for another day…