Football Predictions

Middlesbrough vs Tottenham: FA Cup preview, predictions, possible XIs & live stream

By Harry Edwards

Published: 17:19, 3 January 2020

Tottenham Hotspur quest for a first trophy in 12 years continues when they travel to Middlesbrough in the FA Cup this weekend.

The north London have not tasted glory since the 2008 League Cup and have only reached two finals in the 12 years since, losing the 2009 League Cup final and 2019 Champions League final.

In that time they have also reached four FA Cup semi-finals, most recently in 2017/18 but have also gone out at the fourth round on five occasions. To reach the fourth round this year they will have to get past Championship side Middlesbrough, managed by Jonathan Woodgate who was part of the last Tottenham side to win a trophy.

Boro are currently 16th in England’s second tier but have won their past four games, enjoying a revival after initial calls for Woodgate to be sacked. But can he continue that run with an upset against his former side?

Read on for our Middlesbrough vs Tottenham preview, team news, TV coverage information and more.

Key info for Middlesbrough vs Tottenham – and how to stream live:

Competition: FA Cup

Venue: Riverside

Date: Sunday, 05 January 2020

Kick-off: 2:01 PM (UK time)

TV coverage (UK): BT Sport 1

Live stream: Bet365* are streaming all FA Cup matches live for account holders. Those without a Bet365 account already who are interested in streaming Middlesbrough vs Tottenham live can take advantage of this service by following the simple steps below.

  1. Click on this link
  2. ‘Join now’ and enter details.
  3. Log in and fund the new account.
  4. Pick the desired event from among the ‘live now’ or ‘schedule’ sections in Bet365’s ‘live streaming’ category.

*Geo restrictions apply, 18+ only, must have a funded account, BeGambleAware.

Last five meetings: Middlesbrough vs Tottenham

04 February 2017: Tottenham 1-0 Middlesbrough (Premier League)

24 September 2016: Middlesbrough 1-2 Tottenham (Premier League)

04 March 2009: Tottenham 4-0 Middlesbrough (Premier League)

16 August 2008: Middlesbrough 2-1 Tottenham (Premier League)

12 April 2008: Tottenham 1-1 Middlesbrough (Premier League)

Aggregate Score: Middlesbrough (LLLWD) 4-9 Tottenham (WWWLD)

Ones to watch

Middlesbrough: Rudy Gestede

Having a striker go almost two years without scoring is never great, but when they do finally break their duck it can bring confidence. And that’s exactly what Middlesbrough will hope happens with Rudy Gestede.

The 31-year-old scored in Boro’s 2-0 win over Preston on New Year’s Day, his first goal since February 2018, having really struggled with numerous problems including injury.

But he has featured in Boro’s past five games, earning his first start of the Championship season on Wednesday. With options thin, the former Aston Villa man is likely to start once more against Tottenham and may look to continue his scoring run against a side that has been leaking goals.

Key stat: Rudy Gestede has scored four goals in 14 FA Cup appearances for Middlesbrough, Blackburn Rovers, Aston Villa and Cardiff City.

Tottenham: Son Heung-min

Tottenham have been without Son Heung-min for the past three games but his return from suspension couldn’t come at a better time.

Usually, Jose Mourinho might opt to rest a player of Son’s calibre for an FA Cup third-round tie but the South Korean will need to be bedded back into the side after his absence.

With Kane injured and Tottenham’s squad lacking depth in attacking areas, Son should start on Sunday and will look to return with a bang.

Key stat: Son Heung-min has been directly involved in 18 goals for Tottenham across all competitions this season.

Team news


Middlesbrough opted for a back-three in their recent win over Preston and could choose to stick with that plan in hopes of frustrating Tottenham.

Woodgate is unlikely to want to switch too much of his winning formula, but there could be some minor changes.

Predicted XI: Mejias; Howson, Ayala, Fry; Coulson, Saville, McNair, Johnson; Tavernier; Fletcher, Gestede.

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Tottenham will be without Kane who left St Mary’s on crutches after a suspected hamstring injury in their recent defeat to Southampton. However, Son will be available for selection after serving a three-man ban for his red card against Chelsea.

There could also be a start for Troy Parrott in replacement of Kane but Mourinho may opt for a more experienced side with Lucas leading the line and Erik Lamela also coming in.

Predicted XI: Vorm; Walker-Peters, Foyth, Sanchez, Sessegnon; Skipp, Winks, Lo Celso; Son, Lamela; Lucas.

Squawka prediction

The honeymoon period for Mourinho at Tottenham is well and truly over, and there are already signs of the wheels coming off.

However, it is still far too early for things to turn sour and the Portuguese will be looking forward to an FA Cup tie that could potentially turn attention away from their indifferent Premier League form.

Middlesbrough are on a decent run right now but in the managerial battle between Woodgate and Mourinho, Tottenham should see this one out.

Scoreline prediction: Middlesbrough 1-3 Tottenham