Tottenham's bold bid to challenge the Premier League's top four suffered an immediate setback at Middlesbrough as goals from David Wheater and former Spurs favourite Mido condemned Juande Ramos's side to a 2-1 defeat on Saturday.
Robert Huth's own goal in the second minute of stoppage time, as the German attempted to clear a David Bentley free kick, proved too little too late for the unimpressive Londoners and Ramos must go back to the drawing board after a close-season of costly recruitment.
Wheater again proved his worth in the attacking third with a neat finish past Brazilian goalkeeper Heurelho Gomes 19 minutes from time. And Mido sent his old club crashing to an unlikely defeat with Middlesbrough's second goal in the closing stages.
Ramos handed full debuts to Gomes, Mexican Giovani dos Santos, Croat Luka Modric and Bentley as his new team of nations took shape.
However, the absence of leading scorer Dimitar Berbatov from Spurs' starting line-up suggested the Bulgarian's desired move to Manchester United could still happen before the closure of the transfer window.
Middlesbrough introduced new signing Justin Hoyte prior to kick-off after the England Under 21 full back completed his move from Arsenal earlier in the day.
However fellow new boys, the Frenchman Didier Digard and the Dutchman Marvin Emnes, were named among Gareth Southgate's substitutes.
In the absence of Berbatov, Tottenham employed a lone striker in the shape of Darren Bent with the diminutive dos Santos the most advanced member of a five-man midfield.
Wingers Aaron Lennon and Bentley were clearly under instructions to supplement a threadbare attack and the latter flashed an angled drive beyond Brad Jones' right hand post in the 15th minute.
Middlesbrough winger Stewart Downing had tested former PSV Eindhoven goalkeeper Gomes five minutes earlier and the home team should have gained the initiative in the 18th minute.
Turkey forward Tuncay Sanli raced clear of the Spurs' defence before squaring the ball to an unmarked Afonso Alves 12 yards out. However, the Brazilian hesitated, allowing Tottenham full back Benoit Assou-Ekotto an opportunity to divert a weak shot over the crossbar.
The hosts were beginning to make their presence felt and only a controversial decision by referee Martin Atkinson denied the Teessiders a first half lead.
Downing whipped in a 32nd minute corner and Wheater broke free of marker Michael Dawson before heading beyond Gomes at the far post. However, a wild celebration was short-lived as the defender was penalised for pulling his opponent's shirt.
Alves almost atoned for his earlier miss only to see a crisp right foot shot narrowly clear the crossbar and Gomes was forced to make another low save from his fellow countryman on the stroke of half-time.
Berbatov and Gareth Bale replaced dos Santos and Lennon 25 minutes from time as Tottenham launched a late-bid to steal all three points and the former played in captain Jermaine Jenas with his second touch.
The England international midfielder drew goalkpeer Brad Jones only to shoot weakly at the Australian's feet.
Boro's response was perfect and it was Wheater who tapped home the goal his first half efforts deserved. Downing's cross from the left was deflected onto Gomes' crossbar.
Wheater was on hand to convert at the far post and when Mido added a second against his former club Tottenham's miserable day was complete. Huth's late own goal meant little to either side.
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