Tottenham were knocked out of the Europa League, despite a comfortable victory over Shamrock Rovers in Dublin.
Goals from Steven Pienaar, Andros Townsend, Jermain Defoe and Harry Kane sealed the win, but Rubin Kazan's 1-1 draw against PAOK Salonika rendered Spurs' efforts futile.
Pienaar opened the scoring with a deflected shot before Townsend found the top corner from long range.
Defoe and Kane scored from close range at the end of either half.
The result in Greece meant Tottenham could not progress, no matter how many goals they scored against Rovers but, after making nine changes to his starting line-up, Harry Redknapp will be pleased with the performance of his fringe players.
Youngster Townsend caught the eye on the wing, with his fantastic goal capping a classy performance, while Danny Rose continued his rapid development with an assured display at full-back.
Needing above all to score goals, Tottenham were razor-sharp in the final third, but they did enjoy some luck at the other end of the pitch as both Jake Livermore and Carlo Cudicini escaped red cards for bringing down Rovers players when they were through on goal.
The home side, eager to give a good send-off, enjoyed some good early possession with Ken Oman and Dan Murray going close.
Pienaar's opening goal came against the run of play, and there was an element of luck about it as the midfielder's angled shot took a deflection off James Paterson to beat Richard Brush in the Rovers goal.
There was nothing fortunate about the second goal with Defoe laying it off for Townsend, who placed a first-time shot into the top corner from the edge of the area.
Once they had secured their foothold in the game, Spurs set about boosting their goal difference to overhaul Rubin Kazan in the Group A table.
And once Defoe turned his marker on the stroke of half-time to score a third goal, set up by Townsend, the improbable suddenly became possible.
Unfortunately for the visitors, 10-man Rubin Kazan equalised in Greece early in the second half to take Spurs' fate out of their own hands.
Regardless, they continued to pile forward and were given a reprieve early in the second half when Livermore hauled down Karl Sheppard when the striker was through on goal - only to breathe a sigh of relief when the referee waved play on.
They might have scored a fourth when Sandro's shot hit the past after a defensive mix-up, before another decision went Tottenham's way - Oman was through on goal and brought down by Cudicini, but the Italian was spared conceding a penalty and red card by the linesman's flag.
Both sides traded half-chances as the game became stretched in the final 10 minutes, most notably when Iago Falque hit the post from long range, before 18-year-old striker Kane spun his marker in the final minute of the match to score his first goal for the north London club.
However, it mattered very little to Redknapp's men, who will now hope their elimination helps a sustained title challenge in the Premier League while their rivals - the two Manchester clubs, Arsenal and Chelsea - continue to battle it out on the continent.