Tottenham vs Middlesbrough Betting Tip Over 2.5 goals – 14 January 2020

Spurs to progress from entertaining replay

Jonny Howson /Middlesbrough ©imago images / PA Images 14.01.2020

EnglandTottenham vs MiddlesbroughEngland
14th January 2005hrs
Football – England – FA Cup
Pick Over 2.5 goals
Bookmaker Marathonbet
Odds: 8/13 odds taken 2000 GMT, Monday 13 January

Tottenham had to come from behind in the first game between these two to earn a replay and will be looking to avoid any upset against a Middlesbrough team coached by one of their former defenders, Jonathan Woodgate.

Bet at Marathonbet

Tottenham Preview – Can Mourinho lead his Spurs side to a meeting with Southampton in the fourth round?

An equaliser from Lucas Moura spared Spurs’ blushes 10 days ago as it gave them another opportunity to make it past their Championship opponents and into the next round. Jose Mourinho was clearly expecting a testing encounter and named a very strong side – unlike many of of his Premier League colleagues. He will be thankful he did as Tottenham were pushed all the way but did finish strongly and will feel they could have won it in the end.

Mourinho will once again have to do without Harry Kane who is sidelined for another few weeks with a hamstring injury. His presence has been an obvious miss with Tottenham struggling to take the chances the are creating since he’s been absent.

Our betting prediction:
Tottenham to score in both halves

Bet at Boylesports

(odds taken 2000 GMT, Monday 13 January)

With Spurs now nine points behind fourth placed Chelsea following defeat to Liverpool at the weekend, the FA Cup takes on even more significance in the context of their season. Mourinho knows he is under pressure to bring success to the club following his appointment.

It’s a competition that Tottenham have not won since 1991 whilst their last trophy was 2008. For all the plaudits and achievements under Mauricio Pochettino, there was frustration that they did not win anything. Mourinho himself has only won the FA Cup once during his various spells in English football.


Middlesbrough Preview – Is Jonathan Woodgate set to surprise his former club and knock them out the Cup?

Jonathan Woodgate was thrust into his first senior coaching job during the summer and it’s fair to say it has taking him some time to get to grips with it. Assisted by Robbie Keane, both enjoyed their time when at White Hart Lane and will be looking forward to visiting the new stadium as they attempt to continue what has been their best rest of form to date.

‘Boro are unbeaten in six matches coming into this one with four wins and two draws. They remain some eight points off the playoff positions so have a big job on their hands in the second half of the season if they are to mount a challenge for promotion.

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Middlesbrough have only ever reached the final of this competition once and came up short when losing to Chelsea in 1996/97 at Wembley. Any thoughts of doing similar this time around would be outlandish but Woodgate and Keane clearly value the FA Cup and will be out to cause a shock on Tuesday. They also know that another good performance would see their players’ confidence continue to grow as they hope to prolong their good run of form in the league.


Tottenham vs Middlesbrough Betting Advice

Middlesbrough had the better of the first hour in the first cup tie but Spurs came on strongly when they equalised and showed the quality they had. Mourinho will be demanding that his team start as they left off and don’t give their opponents anymore encouragement. Their need to stay in the cup is greater and expectation is also much higher considering their Premier League status.


Key Facts – Tottenham vs Middlesbrough Betting Tip

  • Spurs spared their blushes with an equaliser at the Riverside in the original tie
  • Mourinho has won the FA Cup once before, when coach of Chelsea in 2006/07
  • Middlesbrough have shown improvement of late and are now unbeaten in six games


Spurs are overwhelming favourites with the bookmakers for this and I would expect them to have too much on the night for their visitors. However, they have been conceding a lot of goals in recent times, failing to keep a clean sheet in their last eight matches. That should give ‘Boro hope who have notched in their last eight overall and all of their last four away games. As such, Over 2.5 goals is the betting tip in this FA Cup replay.


The best betting odds for Tottenham vs Middlesbrough

Tottenham to win: 1/4 at Bet365
Draw: 11/2 at Bet365
Middlesbrough to win: 9/1 at Bet365