Tottenham Hotspurs spent the most out on any Premier League club over the summer transfer window, totaling more than 45 Million pounds, on the likes of Bentley, Modric and Giovanni. Completing a squad which Ramos claims can rival the big four. It was time to put this new squad to the test against a relatively unchanged Middlesbrough team.

Spurs started out brightly, but started to look a bit unbalanced with Bentley playing out on the left wing due to Aaron Lennon claiming both his favored right wing position and number seven jersey. Noticeably absent from the starting Spurs lineup was Berbatov, possibly due to transfer speculation revolving around Manchester United and himself.

Middlesbrough didn't take long to find their rhythm and get back into the game and David Wheater headed the ball into the back of the net only to have it unfairly ruled out because of a supposed foul he had committed.

In the second half Tottenham were starting to look fairly lackluster and the new signings certainly did not seem to be pulling their weight. Ramos switched up the team bringing on Berbatov and Bale which immediately injected fresh life into the Tottenham game. This, however, was shorted lived as Wheater managed to claim a goal, smashing a deflected ball into the open net from close range.

When the ex-Spurs player, Mido, came on and added insult to injury by redirecting the ball home for Middlesbrough's second, Spurs were looking like a team well beaten.

Tottenham did manage to grab a consolation goal in the last few minutes when Bentley's free kick was deflected in by Huth for an own goal, ending the game with a 2-1 score line to Middlesbrough, once again proving that money doesn't always buy you happiness.

Overall match rating: 3 out of 5