Tottenham's aspirations of challenging the Premier League's top four suffered an early setback as Middlesbrough beat them 2-1 at The Riverside. Defender David Wheater scored the first in the 71st minute after an Afonso Alves shot had come back off the underside of the crossbar and Mido, on for Alves, turned in a second with four minutes to go.
All eyes pre-match had been on Tottenham's Dimitar Berbatov, who has been strongly linked with a move to Manchester United, and his appearance as a 65th-minute substitute did not help Spurs take anything from the game.
A late Robert Huth own goal was mere consolation for the Londoners.
It now remains to be seen whether Berbatov will remain a Spurs player, but on the basis of this performance they will certain need to sign a top-quality replacement should he leave if they aim to be Champions League contenders.
Alan Hutton (foot) was not available, so Didier Zokora was set to take up a defensive position.
Midfielder Gary O'Neil overcame a calf strain to start for Boro while Emanuel Pogatetz was included following a knee niggle.
Ramos included four debutants in his line-up after a busy summer of transfer activity at White Hart Lane - goalkeeper Heurelho Gomes, England international David Bentley, Croatian playmaker Luka Modric and Mexican forward Giovani dos Santos.
Giovani and Bentley combined on the quarter-hour as the former Barcelona man wove his way inside from the right flank and nudged it to the England midfielder, whose shot drifted wide of Brad Jones' right-hand post.
Boro defender Robert Huth stretched to cut out an Aaron Lennon cross which looked destined for Darren Bent, and seconds later there was heroics at the other end.
Wheater's ball from the right released Tuncay Sanli and the Turk got away from Benoit Assou-Ekotto who had been left all alone at the back.
Tuncay rolled it across the box to the unmarked Alves who seemed certain to score but Assou-Ekotto somehow managed to deflect the shot over the top.
Tottenham were a whisker away on the half-hour when Zokora's low cross from the right just evaded both Bent and Giovani, with Wheater turning the ball out for a corner.
The big Boro defender thought he had put his team ahead in the 32nd minute but his headed goal was disallowed for tugging Dawson's shirt as he fought to reach Stewart Downing's corner.
Boro looked lively on the counter-attack as Tuncay led another break, but Alves' cross from the right was charged down by Jonathan Woodgate, back to face his old hometown club.
Another shot on the turn from the Brazilian following another fast break was easily smothered by Gomes.
Fabio Capello's England lieutenant Franco Baldini was in attendance ahead of tonight's squad announcement for the Czech Republic friendly next week, and Bentley was doing his best to make a good impression early in the second half, drilling in a right-foot shot which Jones could only parry away.
Assou-Ekotto then made another timely interception to prevent Alves' pass reaching Tuncay after the Brazilian had used his strength to turn away from Dawson.
Woodgate produced a flying block to deny Tuncay's goalbound shot after a Downing corner deflected kindly to him.
Ramos opted to bring on Berbatov in the 65th minute for Giovani to a mixture of cheers and jeers from the Spurs end and his first act was to stab a right-foot ball across the area from the left which did not find a team-mate.
His next contribution was more useful, playing a neat one-two with Jermaine Jenas whose sidefoot shot was blocked by Jones' legs.
Boro took the lead in the 71st minute when Downing crossed from the left and Alves got ahead of his marker at the near post.
His flick was tipped onto the underside of the bar by Gomes but Wheater was on hand to finish the job from a yard out.
Downing almost laid on a second three minutes later, but O'Neil's header from his left-wing cross was easily caught by Gomes.
Bentley was booked for a foul on Alves before Jamie O'Hara replaced Assou-Ekotto for Tottenham.
Bent curled a right-foot shot wide from outside the box which Jones seemed to have covered, and O'Hara almost capitalised when Wheater chested down a ball in but Jones was slow to react.
The game was effectively over when two Boro substitutes combined for the winner in the 86th minute.
French debutant Didier Digard smashed a low ball in from the right and Mido diverted it past Gomes to kill off his old club.
Spurs pulled one back in injury time when Huth headed into his own goal from a Bentley free-kick, but they could not conjure an equaliser.
