Arsenal will again face Bayern Munich in the Champions League's first knockout round following Monday's draw.
The Gunners were handed a repeat of their last-16 ties from both 2013 and 2014, both of which saw them eliminated. They also met in last season's group stage.
Manchester City were paired with Monaco in the first tie drawn out while Leicester were the last team drawn and will face Sevilla.
Arsenal's general secretary David Miles told BT Sport 2: "We thought it might happen, we've played them five or six times in the last 15 years.
"We've now qualified for the knockout stage for the 14th successive season, that's testament to Arsene and the squad over that period.
"The fans will think we've got the rough end of the draw again but at some stage the tide's got to turn so why not this time?"
The ties will be played in February and March, with Arsenal knowing they have the second leg at home by virtue of qualifying as group winners.
"Hopefully we can get some of our injured players back and the home game in the second leg will be vital for us," said Miles. "We're going to be upbeat and positive."
Manchester City's director of football Txiki Beguiristain was happy with his side's draw but warned Monaco - who twice beat Tottenham en route to topping group E - pose a tough test.
"We are happy to be here, and then we have avoided Real Madrid and Barcelona," he told BT Sport.
"Monaco are playing probably the best football in France now. In a group with Tottenham and Bayer Leverkusen they were top and they have young players and a lot of talent.
"It's a new adventure for everybody here and it is a good draw. We want to be offensive and play attacking football and Monaco want this (as well)."