Signed in 1958, Cliff was regarded as one of the best wingers in the world in his heyday and a key player in the double team.
Famed for his high-velocity dribbles down either flank, the Welshman possessed a body swerve that would leave defenders for dead and unmatched courage despite his slender 5ft 7ins frame.
With 159 goals in his 378 appearances, Cliff remains fourth in our all-time goalscoring list behind Jimmy Greaves (266), Bobby Smith (208) and Martin Chivers (174).
Cliff on - Bill Nicholson
"Bill’s whole approach to football was to play the way you train. He said if you train with method and effort that’s how you play, it was all based around and geared around our training and he was the top man at that. He had great schemes of work, and that really came into our game, and that’s how he got the best out of me, he got me into great shape."
Below: Cliff, far left, with the double-winners, 1961
Cliff on - entertaining the fans
"I was always aware of my ability with the ball and when I picked the ball up I sensed an expectancy in the crowd and I just responded to it. For me, to get the ball and go at defenders was something that I just loved doing. It was the main part of my game. I was given a bit of a free role if you like with Bill Nicholson but I still had to do it within the structure of team work."
Cliff on - our first European Cup match at the Lane against Gornik in 1961
"We were four goals down at one point (in the first leg) and we weren’t doing particularly well, we managed to snatch a couple of goals back, but we hadn’t played well and we’d got beaten 4-2. Bill Nicholson wasn’t very happy and we could tell that by the way we trained for the second leg, he really got us up for it.
"We’d taken a bit of stick from the press, quite rightly so, and of course the fans, they were up for it as well and we came out onto the pitch at White Hart Lane, and I have never experienced an atmosphere like it, it was just incredible.
"The Gornik team were intimidated, no doubt about it, because the crowd were virtually on top of them at White Hart Lane, whereas in Poland where you’ve got the running track. The crowd were just absolutely amazing that night and I’ve never experienced an atmosphere like it. We just ran riot and beat them 8-1 - I would say that was probably the best performance by any team that there has ever been, I have to say I got a hat-trick that night which is one reason it’s something that I remember!"
Below: Cliff, from row, second from left, with the Cup Winners' Cup winning team, 1963
Cliff on - winning the Cup Winners Cup in 1963
"It was an amazing performance. Atletico Madrid were highly fancied, a top European side, but we just took them apart, some great performances especially Terry Dyson, that night he scored two of the goals and had probably his best-ever game for Tottenham. He always reminded us of that. He’d always say to us, if anyone had a little go at him about something, he’d always say ‘Hey, remember Rotterdam’, that was his night, and that was our night, we was fantastic."
Cliff on - the double team - was it the best?
"I think so yes, there’s no doubt about it. We had a great mixture of talent and skilful players, the likes of Danny Blanchflower, John White and then you had the power of Mackay and Bobby Smith and the pace of someone like myself, so it was a great blend."
Cliff on - what's so special about Spurs
"The thing about the club is there’s always been a tradition to play attractive, entertaining football, that’s been with the club right through. You take all the teams that have played here, and there has always been that approach to pass the ball and it’s been important to be an entertaining side. That was something that was always impressed upon us by Bill Nicholson, that the fan is the important person, they come through the turnstiles and they’ve got to be given value for money."