A crowd of 64,000 fans were crammed into White Hart Lane on March 10, 1962, to see goals from Cliff, one of the club's all-time greats, and Danny Blanchflower topple Villa 2-0 to set-up a semi-final against Manchester United.
Of course, Bill Nicholson's men would go on to lift the FA Cup again - a 3-1 against Burnley at Wembley - and were unluckily beaten 5-4 on aggregate by Eusebio's Benfica in the European Cup.
Defending their title, the team finished third in the league.
With another FA Cup quarter-final on the horizon, who better than Cliff to rekindle a few memories of those glory, glory days past and talk about the current crop of players determined to write their own history.
So this is the first of our 'week with Cliff', where the Welsh legend who scored 159 goals in 378 games for us between 1958-1968 will talk about the current team, Gareth Bale, the events that shaped our history 50 years ago, the Nat Lofthouse-inspired Bolton team that won the FA Cup in 1958 and what the FA Cup means to him.
MONDAY - CLIFF ON THE SPURS CLASS OF 2012
Cliff is convinced Harry Redknapp's squad can hold on to third place in the Premier League - and book a place at Wembley in the FA Cup.
The team is looking to bounce back from three-successive defeats in the league when Bolton arrive at the Lane for the FA Cup quarter-final on Saturday.
Victory, and we'll be back at Wembley for the semi-finals of the competition.
Cliff has seen every home game this term as he hosts the Legends Lounge on matchdays and he maintains belief that this season's goal - Champions League football - will be attained.
"We've had a tough run of results," said Cliff. "We were poor in the end against Arsenal after going 2-0 up, we all know that.
"But against United, they weren't 3-1 better than us, no way. I thought we were equal to them on the day.
"We're going through a sticky patch but the lads will be up for it on Saturday, no doubt about that. I think we'll snap out of this spell and finish in the top four and we're certainly good enough to hold onto that third place.
"Gareth's a top-class player, Jermain Defoe, Luka in midfield, Scotty, Ledley, Rafa - the team is there, talent all over the pitch.
"Michael Dawson will be a miss because he's a fantastic character and a winner. But we've top players to come in.
"I've been very impressed with Jake Livermore. He's a Tottenham lad through and through, came through the system and now here he is in the Premier League and Harry knows he can play him anywhere."
Tuesday - Cliff on Gareth...