Arsenal’s fall from Champions League stalwarts to Europa League regulars is something that Gunners’ fans won’t want reminding of.
The past three consecutive seasons spent in Europe’s secondary club competition haven’t been particularly kind to Arsenal, with semi and final defeats propping up a measly round of 32 exit.
But undoubtedly the most heartbreaking of the Gunners’ runs in the competition came back in 1999/2000 when Arsene Wenger led his side on quite the journey…
Arsenal entered the UEFA Cup in the Third Round after coming third in their Champions League group behind Barcelona and Fiorentina.
Having struggled in their ‘home’ fixtures at Wembley, the Gunners returned to Highbury and regained their swagger with a 3-0 win over Nantes.
Goals from Marc Overmars, Nigel Winterburn and Dennis Bergkamp allowed for a comfortable win against the French side.
The second leg proved more problematic however.
Once again, Arsenal scored three goals (Thierry Henry, Giles Grimandi and Overmars) but they also conceded three during a uncharacteristically shaky defensive display.
Still, a 6-3 win on aggregate got the ball rolling.
The decisive red card
Deportivo La Coruna were the opponents in the Fourth Round and formidable ones at that.
The Spanish side would go on to win La Liga that season with the likes of Pauleta and Roy Makaay providing the firepower.
A rare Lee Dixon goal and a common one from Henry meant Arsenal were 2-0 up at half-time in the first leg at Highbury.
However, when Brazilian playmaker Djalminha scored a penalty soon after the restart, nerves began to jangle.
Invigorated by the away goal, Deportivo sustained the pressure until their goalscoring hero became the villain.
Djalminha was booked twice in quick succession, once for diving and again for a barge on Grimandi, and was left to vent his frustrations in an early bath.
Smelling blood, Arsenal’s frontline pounced to put the tie beyond doubt.
Henry scored again before Nwankwo Kanu and Bergkamp made it 5-1 — Deportivo’s heaviest defeat of the season.
The soon-to-be La Liga champions won 2-1 in the second leg but Djalminha’s temper had cost them dear.
The Romford Pele makes Germany his own
The quarter-final once again started with a pleasing win at home in the first leg.
Yet another Henry goal previewed Freddie Ljungberg’s first strike of the campaign as Arsenal beat Werder Bremen 2-0 in a game they controlled from start to finish.
The second leg was soured by a controversial second yellow for Henry (not before he scored his sixth goals in as many UEFA Cup games) for which Wenger was sent to the stands for complaining about.
However, not even a impending suspension for the Gunners’ best player could take the shine off the result.
Ray Parlour (aka The Romford Pele) scored a beautiful hat-trick to inspire his side to a 4-2 win on the night and a convincing 6-2 aggregate victory.
It was arguably the poodle-haired midfielder’s greatest night in an Arsenal shirt.
Cometh the hour…
Henry’s absence gave fans a reason to be cautious heading into the semi-final first leg at home to Lens.
But after two minutes Bergkamp reminded the world of his unbridled genius as he deceived three defenders before rounding the keeper to slot into an empty net.
Henry scored upon his return in France and Kanu’s late strike put the result beyond doubt despite Pascal Nouma’s goal for Lens.
3-1 over the two legs and Arsenal were heading to Copenhagen for the final.
Many had hoped the final would be an all-English affair however Leeds were beaten 4-2 on aggregate by Galatasaray.
The tie was overshadowed by the death of two Leeds fans in Turkey which led to Galatasaray fans being banned from the second leg at Elland Road.
Turkish fans clashed with both Leeds and Arsenal fans on the eve of the final in Copenhagen which produced a feverish atmosphere for the game itself.
Played in near-deafening noise the two teams held nothing back but each team’s intensity cancelled the other’s out.
Martin Keown missed Arsenal’s best chance in normal time while David Seaman frustrated Arif Erdem and the mighty Gheorghe Hagi.
As the game entered extra time (which could be ended by a Golden Goal), Arsenal were suddenly made favourites when Hagi was sent off for a clash with Tony Adams.
Overmars and Henry both squandered good opportunities to end the game as the referee blew for penalties after 120 minutes of breathless yet goalless action.
Davor Suker struck Arsenal’s first spot-kick against the inside of the post.
Had he been playing for Croatia it would have undoubtedly nestled just inside the opposite post but his luck was rotten in an Arsenal shirt and the ball scuttled clear.
Galatsaray’s penalties were flawless and when Vieira’s effort cannoned off the crossbar it meant the Turkish side were one strike from glory.
Before the game, Wenger had identified Hagi as the main threat but with the legendary playmaker looking on from the sidelines it was another Romanian Gheorghe who dealt the final blow.
Gheorghe Popescu, formerly of Spurs, smashed his penalty past a despairing Seaman and that was all she wrote.