SERIAL trophy winner Jose Mourinho was brought to Tottenham to end their trophy drought, however, Mourinho and Co may be forced to work had to overcome in-form Middlesbrough in the FA Cup on Sunday afternoon.
The Spurs boss seems intent on climbing the stairs at Wembley again this season, however, since arriving in north London in November the Lilywhites have shown no significant signs of improvement under the Portuguese's stewardship.
The Londoners Premier League season has been plagued with inconsistency and that was once again evident during the festive period as the capital club came unstuck against both Norwich and Southampton respectively.
In stark contrast, Middlesbrough will enter this cup clash brimming with confidence after taking maximum points from their four league outings either side of Christmas.
Consequently, Jonathan Woodagate's men have hauled themselves away for the English Championship basement zone and Boro will aiming to continue their momentum by claiming an FA Cup scalp against star-studded Spurs.
The Betting Odds
A Middlesbrough win and an FA Cup upset will attract plenty of attention from punters at 4/1 (Bet 365) as will the draw which is priced at 3/1 (Bet 365) with the same firm.
Tottenahm make the trip north to the Riverside as odds-on favourites at 4/6 (UniBet) to triumph in this FA Cup third-round showdown.
The Betting Angles
Spurs' recent struggles were further compounded against Southampton on New Year's Day when talisman Harry Kane tore his hamstring and that will force Mourinho into having to mix things up in Tottenham's attack.
However, Son Heung-Min is available for Spurs after serving a three match suspension and if the South Korean superstar gets selected on Sunday then the odds of 8/5 (Sporting Bet) for Son to score at anytime appeal.
Son has scored 10 goals in 17 appearances to date and he showed last season that he is more than capable of leading the line for Tottenham – all of which adds to the appeal of backing the Spurs forward to make the net bulge against Middlesbrough.
One man who could be tasked with trying to shackle Son is Middlesbrough's makeshift defender Jonny Howson and I like the look of the 9/2 (UniBet) that is available for the Boro utility man to be booked.
Howson – a midfielder by trade – has played at both centre-half and right-back in recent times and having picked up six bookings in 22 outings this term, Howson looks overpriced at 9/2 (UniBet) to have his name taken against top-flight opposition in what could be a fiery affair in front of a raucous Riverside crowd.
Indeed, this cup tie looks like a bit of a banana skin for Spurs, however, Mourinho has a tendency to field strong sides in cup competitions and with that in mind, I will be looking to get Spurs on side on Sunday.
Backing a Tottenham win at 4/6 (UniBet) is tempting. however, I'm conscious of Spurs' well-documented difficulties away from home – Spurs have failed to register a Premier League clean sheet on the road in 12 months.
Therefore, I'm going to opt for an alternative angle by utilizing William Hill's Build Your Odds feature by combining Tottenham on the double chance, at least one Tottenham goal, over four Tottenham corners and two or more match bookings which pays 4/5 (William Hill) – a bet that would have banked profit in four of the six wins Mourinho has steered Spurs to thus far.
This FA Cup match between Middlesbrough and Tottenham will be played on Jan 5, 2020 and kick off at 14:01. Check below for our tipsters best Middlesbrough vs Tottenham prediction. You may also visit our dedicated betting previews section for the most up to date previews.
In December 2020 we sadly 
