Arsenal FC 1-3 AS Monaco FC Geoffrey Kondogbia and Dimitar Berbatov put Monaco in charge before Yannick Ferreira-Carrasco's late third as ASM closed on a first quarter-final since 2004.
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• Monaco disciplined in defence and devastating in attack at Arsenal
• Geoffrey Kondogbia (38) and Dimitar Berbatov (53) put Monaco in command
• Alex Oxlade-Chamberlain gives Arsenal late hope (90+1)
• Yannick Ferreira-Carrasco promptly restores Monaco's two-goal cushion (90+4)
• The second leg is on 17 March, with the quarter-final draw three days later
AS Monaco FC are on the verge of a first UEFA Champions League quarter-final since reaching the 2004 final after a clinical performance earned victory at Arsenal FC.
The visitors, in European competition for the first time since 2005/06, conceded only one goal in the group stage and continued that form in north London. Arsenal, eliminated in the round of 16 in each of the past four seasons, enjoyed more possession but Monaco made the most of the ball they did get, breakaway goals either side of half-time from Geoffrey Kondogbia and Dimitar Berbatov putting them in control.
Arsenal substitute Alex Oxlade-Chamberlain briefly revived home hopes, only for Yannick Ferreira-Carrasco to restore Monaco's two-goal cushion in the closing seconds.
Looking to make the quarter-finals for the first time since 2010, Arsenal began brightly, Danny Welbeck turning Elderson in just the second minute but, stretching, shooting too high. Arsène Wenger had clearly instructed his charges to be positive from the outset against the team he coached from 1987 to 1994; Santi Cazorla narrowly failed to supply Welbeck moments later.
Monaco, however, had shipped a mere three goals in their previous 17 matches in all competitions and soon showed exactly why, closing down space in a disciplined central block that Arsenal found increasingly difficult to penetrate. Olivier Giroud did head wide from a corner but in the main Monaco held their hosts at bay.
And then, seven minutes before half-time, came the sucker punch. Welbeck was dispossessed narrowly inside the Arsenal half and João Moutinho squared for Kondogbia. The midfielder's drive was speculative, but a decisive deflection off Per Mertesacker sent the ball flying past the wrong-footed David Ospina.
Arsenal started the second half as positively as they had the first, Giroud nodding Cazorla's free-kick over when well placed – but once more they were undone on the break. Monaco countered at pace, Anthony Martial drawing the defenders before squaring for Berbatov and the former Tottenham Hotspur FC striker made no mistake.
The Gunners should have been back in the contest almost immediately as Danijel Subašić only parried Alexis Sánchez's shot; with the goal at his mercy, Giroud sliced the rebound into the crowd.
For all Arsenal's possession, Monaco were posing the greater threat and clever combination work from Nabil Dirar and Moutinho set Martial in on goal; this time, Ospina was quickly off his line to rebuff him. Wenger introduced the pace of Theo Walcott as his side sought a way through the Monaco rearguard, and Sánchez's incisive pass nearly provided one. Subašić blocked from the substitute, who then inadvertently kept out Welbeck's follow-up.
Arsenal's persistence finally paid off a minute into added time when Oxlade-Chamberlain fired in from the edge of the area. Just as they had a foothold in the tie, however, they let it slip it again; the goalscorer lost possession on the halfway line and Ferreira-Carrasco strode clear to drill past Ospina and confirm a famous win for Leonardo Jardim's men.