Nicholson was looking to rebuild his team following the demise of the 'Double' team and as he had done the previous year with Watford, Jennings stepped straight into the Spurs team in place of Bill Brown. His debut was in a 2 - 0 win over Sheffield United on the opening day of season 1964-65.
Initially, Nicholson must have had doubts about Jennings as he took time to settle and during his first two seasons he shared goalkeeping duties with Brown. By the start of 1966-67 Jennings had made the position his own and after a few months Brown was allowed to join Northampton Town. For the next eleven seasons Jennings was first choice goalkeeper at White Hart Lane. He helped the club to win the FA Cup in 1967, the League Cup in 1971 and 1973 and the UEFA Cup of 1974. His total of almost 600 League and Cup appearances is littered with numerous match winning performances and a goal having scored in the 1967 Charity Shield game against Manchester United at Old Trafford.
He will always be remembered for the size of his hands which enabled him to come out to catch a cross using only one hand. His two penalty saves at Anfield as Spurs earned a 1 - 1 draw in 1973 are part of Spurs legend and after a UEFA Cup game in Switzerland Spurs returned with a resounding 5 - 1 victory over Grasshopper Zurich but it was Jennings who received all the plaudits for his performance that evening.
It was only in his last season that Jennings was troubled by injury and as Spurs were relegated manager Keith Burkinshaw made the unbelievable decision to release Jennings in favour of his young understudy, Barry Daines. Jennings moved to Arsenal and gave them years of outstanding service before returning to Spurs to keep fit for the 1986 World Cup Finals. He retired on his forty first birthday as Northern Ireland were eliminated from the competition by Brazil.
On retiring he took on the role of goalkeeping coach and is still involved with the club in their corporate facilities. Pat Jennings was recently honoured by UEFA for winning over 100 international caps for Northern Ireland.
The manager of Watford at the time of Jennings' transfer to Spurs was Ronnie Burgess who had joined in 1936 and played over 450 League and Cup games as well as being captain of the 'Push and Run' side which won the 2nd Division and 1st Division titles in consecutive seasons from 1949 to 1951. He joined Swansea in 1954 and moved to Watford as manager in 1959.
Tommy Harmer, was known as 'The Charmer' and as a player he spanned the years between the 'Push and Run' team of the 1950s and 'The Double' side of the 1960s but missed out on both. He joined Spurs as an amateur in 1948 and made his debut in September, 1951 against Bolton. He played 222 League and Cup games before signing for Watford in October, 1960 having lost his place in the first team to John White. He was loved by supporters with supreme tricks and skills on the ball. Lightly built in the rugged midfield battle of those days he was frequently the inspiration for Spurs best performances having taken over from Eddie Baily as the creative influence in the team. He was at his best in Bill Nicholson's first game as manager, when the new manager restored him to the team. He was the creator behind the 10 - 4 win over Everton and even managed a goal for himself. At first, Nicholson tried to play both Harmer and White in his team but eventually opted for the Scot.
In the book about the late John White, 'The Ghost of White Hart Lane', Harmer is described as, 'though he was small, he was a giant' and Julian Holland wrote, 'Harmer was a truly great player. His tragedy was that his gifts were never fully suited to the type of play current at Tottenham. Under Rowe he was too static. Under Anderson he was denied colleagues quick and responsive enough to turn his genius into Champion-ship winning football. Under Nicholson he lacked the mobility that the new manager looked for. Nor could he supply rapid improvisational touches that Nicholson knew were necessary to overcome planned, coherent defences in 1961.'
Harmer spent two years with Watford before moving to Chelsea as a player/coach and helped them win promotion.
Dennis Bond was a young midfield player who made his name with Watford making over 100 appearances before signing for Spurs in March, 1967 for £20,000. He had made his debut for the Vicarage Road club at the age of seventeen when Burgess was manger. He failed to make an impact with Spurs and only made 26 League and Cup appearances in three seasons, scoring once. He then joined Charlton for £25,000 where he became a regular for three seasons and returned to Watford and made another 200 appearances for the club.
Roy Low has a place in Tottenham record books as the first player to appear for the club as a substitute. It was on 11th September, 1965 when he replaced the injured Derek Possee against Arsenal at White Hart Lane. Low was a wing half but he only made eight appearances and scored one goal in his three years at the club. He joined Watford in February, 1967.
Many well known Spurs players have played for Watford after leaving Spurs. Gerry Armstrong, while not making any great impression in his five years at Spurs, signed for Watford in November, 1980 and went on to greater things in Spain and with Northern Ireland.
Mark Falco enjoyed greater success at Tottenham having come through the youth system and was a member of the UEFA Cup winning team of 1984. He joined Watford in October, 1986 and later played for Glasgow Rangers, Queen's Park Rangers and Millwall. Falco scored 90 League and Cup goals for Spurs and was one of the successful penalty takers in the UEFA Cup Final shoot-out.
From the same era, Paul Miller had developed as an apprentice with Spurs and spent over twelve years at the club before moving to Charlton Athletic in February, 1987. He played over 200 League games and was a regular in the successful Keith Burkinshaw teams of the early 1980s contributing the away goal against Anderlecht in the UEFA Cup Final.
Steve Hodge who had a short time with Spurs in the mid-80s, having joined from Aston Villa in December, 1986, returned to his first club, Nottingham Forest, in the summer of 1988. He later played for Watford towards the end of his career.
Tim Sherwood started his career with Watford and after playing for Norwich City and Blackburn, captaining them to the Premiership title, he joined Spurs in February, 1999. He spent four years with the club, making 93 League appearances, before moving to Portsmouth. He is currently in charge of Spurs Development squad.
The first player to play for both Spurs and Watford was Bill Lane. He was a centre forward who spent less than three years with the club from 1924 but only made 29 appearances before joining Leicester City. He later played for Watford from 1932 to 1936.
Another player from the 1920s who played for both teams was Jack Elkes. He joined Spurs from Southampton in 1922 and was a forward who could also play at centre half. He made over 200 League and Cup appearances for the club and moved to Middlesbrough in 1929. He joined Watford in 1933 spending one season with the club.
John Moran was a full back who had one season with Tottenham, playing twelve matches and then became the first player to be transferred directly between the two clubs by joining Watford in 1932 where he spent four years.
A number of players from the 1950s turned out for both clubs - Bobby Cook, Dennis Uphill, Chris Adams, Johnny Gavin, Alfie Stokes and John Ryden. Ryden, a centre half, had captained Spurs for a season in the mid-50s but the arrival of Maurice Norman and Dave Mackay reduced his opportunity for first team appearances. Stokes scored 40 goals in 65 League appearances but was allowed to join Fulham in 1959 as Bill Nicholson put together his new team.
The 1990s also throws up numerous players who spent time at White Hart Lane and Vicarage Road - Mark Robson and Danny Hill, Darren Caskey, all on loan, Ronnie Rosenthal, Espen Baardsen, Allan Nielsen, Ramon Vega and Stephen Kelly and Andros Townsend (both on loan).
Mark Yeates, a former Tottenham player who came through the youth system, is currently in the Watford team. He made his debut for Spurs on the closing day of the season in May, 2004 setting up a goal for Robbie Keane. He made three League appearances and after a series of loan periods he joined Colchester United in 2007. After two seasons he joined Middlesbrough and then moved to Sheffield United. He joined Watford last summer and has scored three League goals this season from midfield.
Speaking ahead of the Cup tie, Yeates commented on his time at Spurs,
" Tottenham was a big part of my life ...... so I've got a lot of fond memories. I've still got a lot of pals there. Martin Jol gave me a few run-outs, but Spurs are such a big club and at the time in every transfer window they were bringing in three or four new players. It was hard for the likes of myself, Dean Marney and Johnnie Jackson, we were on the fringes. Eventually we had to move on but there are no hard feelings."