Harry Redknapp saw his Portsmouth side beaten 3-1 by Tottenham at White Hart Lane for whom Mido scored a decisive 85th minute penalty.
It could all have been so different for Pompey, who took the lead through a sublime goal from Tresor Lomana Lua Lua, but the match hinged on referee Uriah Rennie's decision to award a penalty for handball by Gary O'Neil who was attempting to block a free kick from Andy Reid.
With the score at 1-1, Portsmouth were rightly incensed but Mido stepped up to convert the spot kick despite the best efforts of Pompey's impressive goalkeeper Jamie Ashdown.
Ledley King equalised ten minutes into the second half before substitute Jermain Defoe put some gloss on the score line with a third a minute from full time.
While Redknapp made three changes to his inherited side with Vincent Pericard, recently recalled from a loan spell at Sheffield United, starting as a lone front runner, opposite number Martin Jol's optimism was evident as he made no changes for the fourth match in succession.
Predictably it was the home side who made the better start. Pompey defender Linvoy Primus played Robbie Keane onside after just three minutes but the Irishman could not take full advantage after shooting straight at Ashdown.
Edgar Davids played in Mido for a similar shooting opportunity but like his strike partner before him he shot straight at Ashdown.
Pompey's defence was ragged and an ever better chance came the way of Keane when played through by Jermaine Jenas but Ashdown stood up well to deny him with Dejan Stefanovic clearing the remaining danger.
Remarkably having failed to make any headway in the match and yet to register a shot in anger Pompey striker Lua Lua struck Spurs with a bolt from the blue.
The DR Congo striker beat Lee-Young Pyo to O'Neil's looped pass and unleashed a right-footed effort from fully 25 yards - the ball whistling past Paul Robinson's left hand and into the back of the net.
Pericard could have doubled the unlikely lead but dallied while a free kick from Jermaine Jenas was fired over as much of the early Spurs impetus was lost.
Davids sought to cajole his team-mates and fired over in a fast and frenetic start to the second period while Pericard, more assured on this occasion, tested Robinson.
Tottenham drew level five minutes later after King got a yard on Primus to nod in Michael Carrick's corner.
At the other end Pericard fed in Matthew Taylor whose first time left shot appeared destined for the top right hand corner but for a breathtaking save from Robinson.
Mido headed over from Wayne Routledge's cross and Jenas also scuffed a presentable opening. Having levelled the score King had to be equally alert at the other end to prevent Pericard connecting with Taylor's expertly driven cross.
Portsmouth were growing as an attacking threat as the game approached its dying embers. Stefanovic almost headed a winner but his effort was blocked by his own team-mate Lua Lua.
Moments later and Pompey conceded a penalty in the most questionable of circumstances. Substitute Andy Reid, on the pitch a matter of seconds struck a free kick which hit struck the jumping O'Neil's arm. Rennie had no hesitation in pointing to the penalty spot and Mido picked his spot although Ashdown diving low to his left was unfortunate to concede.
Substitute Defoe added a late third against his former manager at West Ham and Redknapp will be left to muse on Pompey's fifth straight defeat which leaves the club six points adrift of safety.
