Middlesbrough only lost out to Harry Kane’s second-half penalty in a 1-0 defeat to Tottenham Hotspur at White Hart Lane.
Kane slotted in after Son Heung-min was brought down by Bernardo Espinosa with the hour-mark fast approaching.
Spanish striker Alvaro Negredo was first to show for the visitors when heading over an Adama Traore cross from the right.
But their opponents were regularly slick in possession and Son’s low drive called Victor Valdes into action before Toby Alderweireld headed onto an upright.
More decent work from Son then allowed Kane to head over before his next cross was turned into the net by the England striker – but from an offside position.
Christian Eriksen was also thwarted by Valdes following the break, although Kane was to open the scoring from the spot after Bernardo took down Son inside the area.
However, Boro actually saw late opportunities with Negredo missing with an overhead kick while substitute Patrick Bamford had an effort deflected away before Marten de Roon dragged wide.
Tottenham Hotsour: Lloris, Walker, Dier, Alderweireld, Davies, Dembele, Wanyama, Eriksen, Alli (Winks 88), Son Heung-min (Sissoko 81), Kane (Janssen 90)
subs (unused): Vorm, Onomah, Wimmer, Carter-Vickers
Goals: Kane (pen 58)
Middlesbrough: Valdes, Bernardo, Chambers, Gibson, Fabio, de Roon, Clayton, Forshaw (Guedioura 62), Traore (Bamford 79), Negredo, Downing (Stuani 62)
subs (unused): Ayala, Leadbitter, Guzan, Gestede
Ref: M. Clattenburg
Att: 31,949
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