Tottenham Hotspur's bold bid to challenge the Premier League's top four suffered an immediate setback at Middlesbrough, who were on target through David Wheater and former Spurs favourite Mido to condemn their visitors to a 2-1 defeat. 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 Londoners, and manager Juande 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 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 promise Giovani dos Santos, Croatian playmaker 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 U-21 right-back completed his move from Arsenal earlier in the day. However, fellow new boys, French midfielder 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 keeper 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, nicely positioned 12 yards out. The Brazilian hesitated, though, allowing Benoit Assou-Ekotto an opportunity to divert a weak shot over the crossbar.
Boro were beginning to make their presence felt, and they then had a goal disallowed. Downing whipped in a 32nd-minute corner and Wheater broke free of marker Michael Dawson, before heading beyond Gomes at the far post. His wild celebration was, nevertheless, 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 compatriot 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 Boro keeper Brad Jones towards him, only to shoot weakly at the Australian's feet.
Boro's response was perfect and it was Wheater who tapped home the goal his efforts deserved. Downing's cross from the left was deflected on to Gomes' crossbar, and the defender was on hand to convert at the far post.
When Mido added a second shortly later, his former employers' miserable day was complete, although Huth's late own-goal did reduce Middlesbrough's winning margin.