Cliff joined us from Swansea in February, 1958 and made his debut against Arsenal at Highbury on February 22, 1958.
He was a key member of Bill Nicholson's glory, glory team that won the double in 1961, the FA Cup in 1962 and European Cup Winners Cup in 1963. He won the FA Cup again in 1967.
On October 9, 1968, Cliff pulled on the white shirt for the 378th and final time in a First Division clash against the newly-crowned European champions.
“It was on a Wednesday night under the lights at the Lane, we drew 2-2 and I scored the equaliser,” said Cliff.
“The following morning, I was transferred to Fulham as Bobby Robson’s first signing, he’d just taken over as manager.
“It was almost the final kick of the game and therefore just about my last kick as a Tottenham player. Alex Stepney was in goal for United and I smashed it past him.
"I'd had some great games against United down the years but that's the one I most remember.
“It was quite an emotional night as I’d had 10 wonderful years at Spurs. I was so pleased that it ended that way - what a way to go!”
Below: The programme cover from Cliff's final game for us against United