In a turn of fate, Cliff hits the 80 mark on North London derby day and he made his Spurs debut against the Gunners at Highbury back in February, 1958!
Seen as the best winger in the world in his heyday, Cliff was one of the entertainers of the famous 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.
Indeed, many point to his bravery as his greatest asset and Cliff was never afraid to throw himself in where the boots were flying if he had half a chance of getting the ball or scoring a goal - and he had the injuries to show for it.
Capped by Wales at 18, Cliff starred for home-town team Swansea before a £35,000 deal took him to Spurs in February, 1958.
It wasn't the brightest of starts for Cliff though and after enjoying Wales' run to the quarter-finals of the 1958 World Cup - ended by Pele's Brazil - he broke his leg in the pre-season of 1958-59.
But he came back stronger than ever to play a key role in the ‘glory, glory years’ of the early 1960s.
Cliff thrilled the crowds as we claimed the league and FA Cup double in 1961 – he scored 19 goals in 35 appearances in both competitions - followed by the FA Cup again in 1962 and European Cup Winners Cup in 1963.
A constant in the Welsh side throughout his career, Cliff added the FA Cup to his collection in 1967 before being the last member if the double side to leave to club, a cut-price move to Fulham, aged 33, in 1968 having made 378 appearances for us.
With 159 goals, Cliff remains fourth in our all-time goalscoring list behind Jimmy Greaves (266), Bobby Smith (208) and Martin Chivers (174).
He's 80 today, but is still a regular Matchday Host with fellow legends at the Lane.