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Can Jose Mourinho finally end the drought of the Tottenham trophy?

If you are a Tottenham Hotspur fan, you support one of the top clubs in the English game – at least if you measure that factor on the basis of the honors board.

Their number of 17 trophies is improved by only a handful of clubs and comes to about one big success every eight years in their 138 year existence.

Yet there is a generation of fans who are entering adulthood and have never really had the pleasure of seeing large silverware on the side of North London.

Tottenham Hotspur has not won a big trophy since the League Cup was lifted in 2008

Tottenham Hotspur has not won a big trophy since the League Cup was lifted in 2008

You should not have been born much later than the turn of the century to vividly remember the 2008 League Cup final, with extra effort from Jonathan Woodgate who captured a 2-1 win over Chelsea for Juande Ramos’ side at Wembley.

Since then, there have been near-accidents with two more League Cup finals, as well as last season’s Liverpool League defeat, still painful memories of the club’s worst post-war drought.

Off-form Spurs are far from the pace in the Premier League, its outsiders rank to repeat another point to a Champions League final and were dumped out of the League Cup long ago in a humiliating loss at Colchester United.

Jonathan Woodgate scored the winning goal in the 2-1 triumph over Chelsea at Wembley

Jonathan Woodgate scored the winning goal in the 2-1 triumph over Chelsea at Wembley

Jonathan Woodgate scored the winning goal in the 2-1 triumph over Chelsea at Wembley

The last trophy winning manager Juande Ramos (left) from Spurs has invented their success in 2008

The last trophy winning manager Juande Ramos (left) from Spurs has invented their success in 2008

The last trophy winning manager Juande Ramos (left) from Spurs has invented their success in 2008

ENCOURAGEMENTS

English league (2): 1950-51, 1960-61

FA Cup (8): 1901, 1921, 1961, 1962, 1967, 1981, 1982, 1991

League Cup (4): 1971, 1973, 1999, 2008

UEFA Cup winners Cup (1): 1963

UEFA Cup (2): 1972, 1984

As such, the FA Cup is realistically the last game they can win to prevent the trophy drought from extending to 2021, and they will have serious hope to lift the cup for the first time since 1991.

Their first hurdle to try to put an end to that long wait for cup glory? Of course, it is their most recent Wembley hero Woodgate himself who will welcome his former club at the Riverside Stadium when the former Middlesbrough defender will host Jose Mourinho’s outfit in the third round on Sunday.

Injuries prevented Woodgate from establishing himself as a true favorite on White Hart Lane, but he will always be happy to be remembered for his contribution to the 2008 final, which was only his fourth game for the club, which had joined a month earlier .

His goal covered a strong Spurs performance that saw them coming in from behind to defeat Chelsea who had taken the lead through a free kick by Didier Drogba. Dimitar Berbatov’s penalty brought Ramos’ team level into the second half.

Woodgate holds the trophy cup and man in only his fourth game for Spurs

Woodgate holds the trophy cup and man in only his fourth game for Spurs

Woodgate holds the trophy cup and man in only his fourth game for Spurs

But now Woodgate wants to shoot his former team as Middlesbrough boss in the FA Cup

But now Woodgate wants to shoot his former team as Middlesbrough boss in the FA Cup

But now Woodgate wants to shoot his former team as Middlesbrough boss in the FA Cup

In extra time, Spurs struck as Petr Cech’s attempts to hit the ball bounced the ball from Woodgate’s face into the Chelsea net.

The battle qualities shown that afternoon are in stark contrast to the current team that seems to be limping from one disaster to the next in a scorching campaign.

Yet in that season of 2007-08, Spurs also went through the Premier League turmoil – after firing a popular manager to make way for a highly regarded Iberian appointment. Sounds familiar?

While Ramos was replacing Martin Jol, Mourinho entered Mauricio Pochettino, who could never win over Spurs when it came to delivering trophies.

Tottenham has dropped to three final defeats since the record of the Champions League final of 2019

Tottenham has dropped to three final defeats since the record of the Champions League final of 2019

Tottenham has dropped to three final defeats since the record of the Champions League final of 2019

Spurs is aiming for a FA Cup victory under Jose Mourinho but has not won it since 1991

Spurs is aiming for a FA Cup victory under Jose Mourinho but has not won it since 1991

Spurs is aiming for a FA Cup victory under Jose Mourinho but has not won it since 1991

Mourinho’s career is littered with great silverware – he has won three more trophies than Tottenham ever – but can he end their long wait for success?

He has a better team than Ramos, whose Spurs team was six points worse off in 2008 after 21 games than where they are today.

But the magic of Ramos was in the League Cup and ensured a famous 5-1 win over Arsenal in the semi-final before he saw another rival in Chelsea in the final. It was a rare moment in the club’s recent history to conquer the best sides of England deep in a cup competition.

Spurs excelled in the Premier League under Pochettino, but there was always the feeling that they had serious cases of an inferiority complex in the crunch games against rivals.

Spurs undergo a peak season and fell to a terrible loss on New Year's Day in Southampton

Spurs undergo a peak season and fell to a terrible loss on New Year's Day in Southampton

Spurs undergo a peak season and fell to a terrible loss on New Year’s Day in Southampton

Despite experience with the landing of silverware, Mourinho has a difficult task to improve Spurs' fortune

Despite experience with the landing of silverware, Mourinho has a difficult task to improve Spurs' fortune

Despite experience with the landing of silverware, Mourinho has a difficult task to improve Spurs’ fortune

They offered nothing for purpose in the loss of the Champions League by Liverpool, and were also meek in their other most recent final, which fell 2-0 against Chelsea in the 2015 League Cup final – coincidentally managed by Mourinho.

The side of Pochettino also failed in FA Cup semi-finals against the Blues and Manchester United in 2017 and 2018 respectively – increasing their number of consecutive semi-final defeats to seven, a record of the FA Cup.

Mourinho has won trophies at every club he has been with since his groundbreaking tenure at Porto in the early 2000s, but trying to turn Spurs’s trust into a team of winners can be one of his most difficult tasks to date .

A spineless capitulation to fall 1-0 in Southampton on New Year’s Day offered little hope in the hope that the Portuguese boss could turn the club’s fortune quickly.

Mourinho was Chelsea's manager when he denied Spurs success in the 2015 League Cup final

Mourinho was Chelsea's manager when he denied Spurs success in the 2015 League Cup final

Mourinho was Chelsea’s manager when he denied Spurs success in the 2015 League Cup final

Tottenham fans hope that Mourinho can replicate this FA Cup success from 2007

Tottenham fans hope that Mourinho can replicate this FA Cup success from 2007

Tottenham fans hope that Mourinho can replicate this FA Cup success from 2007

Mourinho won the FA Cup only once, in a 1-0 win over Manchester United in the inaugural final at the new Wembley in 2007, but holds the world’s oldest cup competition in dear esteem and claims it is “very, very special” .

He also claims to understand the supporters’ love for a competition that Spurs has won eight times in their history. It contrasts with the words of Pochettino while he was in charge in North London who claimed that winning cups “only builds egos.”

Right now, an ego is what Spurs needs when they look to shake off a tag of eternal chokers. They now have one of the best managers in the industry to build a winning mentality, but if he can’t, who can?

Anyway, a Wembley hero who helped Spurs 12 years ago win a dream cup could now be in place to hand out a nightmare because his Middlesbrough side hopes to take advantage of a Tottenham turmoil.

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