Arsene Wenger was leading the Gunners against his old club for the very first time in what was their best draw on paper in the Champions League Round of 16 for five seasons.
After losses to Bayern Munich at this stage over the past two campaigns, and premature exits at the hands of Barcelona and AC Milan prior, Monaco was seen as a much more comfortable draw for the north Londoners.
However, that notion was put to bed as Leonardo Jardim's side, who scored just four goals in the group stage, netted on three occasions away from home.
Promising French midfielder Geoffrey Kondogbia opened his Champions League scoring account when letting rip from range in the 38th minute with the ball taking a deflection off Per Mertesacker, leaving Gunners keeper David Ospina rooted to the spot.
Early in the second half, Arsenal were on the attack and looking for a leveler but it worked against them as some sloppy defending allowed Dimitar Berbatov some time and space in the 53rd minute, inviting the former Tottenham star to sink his boot into the ball inside the area for a second.
The tie appeared to be beyond doubt but Arsenal substitute Alex Oxlade-Chamberlain produced a moment of magic when controlling outside the area before curling delightfully into the top left corner in the first minute of injury-time.
But any glimmer of hope that Wenger's side had mustered soon faded when Monaco sub Yannick Ferreira-Carrasco dispossessed Oxlade-Chamberlain on the halfway line before racing beyond the midfielder and slotting past the outstretched right hand of Ospina.
It was a clinical performance from Jardim's Les Rouges et Blancs who will return to Monaco with plenty of confidence for the return bout at the Stade Louis II on March 17.
2014/15 UEFA Champions League - Round of 16 first leg
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