Spurs last game at Watford was in the Carling Cup in December, 2008 at the 5th Round stage. They progressed to a semi-final tie against Burnley with a 2 - 1 success through goals from Roman Pavlyuchenko and Darren Bent.
Spurs found themselves a goal behind within fifteen minutes as Watford mounted sustained early pressure. They drew level on the stroke of half-time with a Pavlyuchenko penalty following a foul on Jermaine Jenas. Spurs scored the winner with fifteen minutes remaining when substitute Bent latched on to a ball from Pavlyuchenko to score with a low shot.
FA Cup 3rd Round
The last meeting between the two clubs in the FA Cup was in January, 1999 when Spurs won 5 - 2 at White Hart Lane. Watford who were in the 1st Division at the time took the lead in the opening minute. Steffan Iversen equalised on ten minutes as Spurs scored three times in seven minutes. Three minutes later Darren Anderton scored with a penalty for handball following a free-kick awarded for a foul on David Ginola and then Iversen added his second on seventeen minutes. Watford showed spirit and pulled a goal back after half and hour but Allan Neilsen restored Spurs two goal advantage three minutes before the interval.
It was not until four minutes from time that Ruel Fox completed the scoring with Spurs' fifth. Two former Spurs players were included among the Watford substitutes that day, goalkeeper Chris Day and Ronnie Rosenthal. Rosenthal came on at half-time, receiving a warm welcome from the Tottenham faithful.
League Cup (Coca Cola Cup) 2nd Round
This tie was played over two legs with the first game at Watford in September, 1994. It marked Jurgen Klinsmann's debut in Cup football in England and he didn't disappoint scoring a first half hat-trick on the ground where he had made his first Spurs appearance in a pre-season friendly the previous August.
The second leg at White Hart Lane a fortnight later in October, 1994 was just as exhilerating as Watford came out victorious by 3 - 2. Spurs, however, progressed to the next round with an aggregate win of 8 - 5. Watford went ahead after fifteen minutes but Nicky Barmby who missed the first match equalised after half an hour. Watford regained the lead early in the second half but Klinsmann again drew Spurs level only for the visitors to score the winner fifteen minutes from time. This was Spurs fourth consecutive home defeat and Ardiles was under increasing pressure.
FA Cup Semi-Final
Spurs were progressing serenely towards the Wembley Final when they met Watford at the FA Cup semi-final stage at Villa Park in April, 1987. The match proved remarkably easy for Spurs who were facing a Watford side who had to find emergency goalkeeping cover due to injury. The 4-1 victory did not flatter Spurs as David Pleat’s side continued their good form and won through goals from Steve Hodge (2), Clive Allen and Paul Allen. Coventry City were their unexpected opponents in the Final and unfortunately that match didn't go as expected.
League Cup 2nd Round
In September, 1975 Spurs visited Vicarage Road for a Cup match for the first time. They won against the 4th Division side through the only goal scored by Chris Jones. Having avoided relegation with victory over Leeds United in the last game of the previous season, Terry Neill's team, in his only full season in charge of the club, progressed to the semi-final stage where they lost out to Newcastle United.
FA Cup 3rd Round
In January, 1939 Spurs were playing in the 2nd Division while Watford were in the 3rd Division (South). An emphatic win at White Hart Lane saw Spurs create another 'first' to include in their record books. It was the first time that numbers were worn on the players' shirts, something which the Spurs directors had been campaigning for over a considerable period of time.
The Spurs goals were scored by Ralph Ward (pen), Fred Sargent, Willie Hall (2), Andy Duncan, Les Miller (2).
FA Cup 2nd Round
Spurs were the Cup holders when the clubs met in January, 1922 with Spurs in the 1st Division and Watford in the 3rd Division (South). Tottenham had overcome Brentford in the 1st Round and a Bert Bliss goal at White Hart Lane was sufficient to see them progress on this occasion. Their defence of the FA Cup came to an end in the semi-finals when they lost to Preston North End in controversial circumstances.
Spurs first FA Cup tie was in October, 1894 when they met West Herts at their old Northumberland Park ground. Four years later, in 1898, West Herts and Watford St. Mary's merged to form Watford FC. Spurs won 3 - 2 with goals from Peter Hunter and Donald Goodall (2) and Tottenham's experience with the FA Cup had commenced.