Tottenham Hotspur 2–1 Manchester City on 16 May 2009

A late penalty from Tottenham striker Robbie Keane extinguished Manchester City's European hopes despite a brave rearguard action by the visitors.

Jermain Defoe capped a vibrant opening period for Harry Redknapp's men with an audacious back-heeled opener.

City hit back when sub Valeri Bojinov rifled home a Benjani knock-down to claim his first goal for the club.

But Keane beat Shay Given from the spot late on after Micah Richards had brought down Fraizer Campbell.

The victory maintains Harry Redknapp's hopes of guiding Tottenham to a Europa League place, an achievement that would represent a remarkable turnaround in the fortunes of a club languishing at the foot of the Premier League table when he arrived last October.

But for City Europe is now beyond reach, potentially undermining the club's leverage in the summer transfer as well as raising the temperature on manager Mark Hughes.

Dispensing with the cautious approach that yielded a point at Goodison Park last time out, Redknapp fielded three forwards, with Keane tucked in on the left side of midfield behind Defoe and Roman Pavlyuchenko.

The initial result was an unfettered attacking display that had City goalkeeper Given working overtime.

At the forefront of Tottenham's early enterprise was Defoe, who had an effort ruled out for offside before forcing two sprawling saves from Given, who also got down well to a Pavlyuchenko effort.

The inevitable breakthrough for Tottenham came with the half-hour mark approaching, Jermaine Jenas feeding Tom Huddlestone, whose sweeping cross was impudently back-heeled in by the airborne Defoe.

A strange sub-plot to the period surrounding Defoe's opener was the absence of City midfielder Elano, who left the visitors with ten men after departing the field with an eye problem.

How far his presence would have altered events is debatable, however, for City's impact on the opening half was negligible.

Their only first-half chance fell to Felipe Caicedo, but the Ecuador striker's weak effort was comfortably gathered by the Tottenham goalkeeper Heurelho Gomes.

With the interval approaching Keane spurned two opportunities to stretch Tottenham's lead, first from a Benoit Assou-Ekotto cross that should have been cut out by Richard Dunne and then when he failed to connect with a volley after chesting down Huddlestone's lobbed pass.

City regrouped at the break, but had nothing tangible to show for their efforts until Hughes made a double substitution in the shape of forward pairing Bojinov and Benjani.

Within minutes City were level, Benjani nodding down for Bojinov, who gleefully drove home his first Premier League goal.

Suddenly, Tottenham were on the back foot, their first-half verve a distant memory.

But with the final whistle beckoning, Richards bundled over Campbell, leaving Keane to send Given the wrong way from the resulting penalty.

A lively finale saw Benjani waste a golden opportunity to equalise when he headed over from inside the six-yard box, while Defoe sent a sliding effort narrowly wide.

But it was not to be for City, who must now come to terms with the end of their European dream while Tottenham contemplate a final-day visit to Liverpool in the race for seventh place.

Tottenham manager Harry Redknapp:
"We dominated the first half and came in at half-time feeling we should have been out of sight.

"In the second half we never got going and lost our way a bit.

"But we got the penalty in the end and I thought it was nailed-on because the lad clambered all over him. We've been on a great run."