Pep Guardiola's men brushed aside the competition in Group G to finish top of the section, while their hosts sneaked into second place in Group A behind Bayern Munich.
Capitalising on Manchester United's prolonged misfortune, Danish upstarts Copenhagen only gleaned one point from their opening three Champions League affairs in 2023-24, but an unforeseen three-match unbeaten run from November to December earned Jacob Neestrup's men a ticket to the last 16.
Slender successes over Man United and Galatasaray came either side of a creditable goalless draw with group winners Bayern, and the German champions' matchday six beating of the Red Devils ensured at least a place in the Europa League for Copenhagen, who lengthened their top-tier European journey as Lukas Lerager struck the only goal against Galatasaray.
Only once before have the Nordic outfit competed in the knockout stages of the Champions League, coincidentally losing to English opposition in the form of Chelsea in the 2010-11 last 16, suffering a 2-0 home loss before clinging on for a creditable away draw at Stamford Bridge.
Thirteen years later, Copenhagen's second bite at the knockout cherry arrives at a time where inconsistency has plagued them domestically, as they entered the Superliga winter break on the back of a three-match winless run, dropping to third in the table on account of back-to-back losses to Viborg and AGF.
The mid-season Atlantic Cup then took centre stage for Copenhagen earlier this month - a tournament comprising teams from various nations with no league commitments at the start of February - but Neestrup's men had to settle for fourth place in the competition, taking six points from an available nine.
The Man City faithful may have shared a joke among one another when witnessing their bitter rivals go down 4-3 to Copenhagen during the group phase, but there will be no time for niceties on Tuesday evening, as the reigning Champions League holders bid to slay another foe during their standard second-season surge.
RB Leipzig, Young Boys and Red Star Belgrade would be the teams attempting to quell the Guardiola juggernaut in the group stage of Europe's premier competition, but their efforts were fruitless, as the Manchester titans breezed into the last 16 with a maximum total of 18 points on the board.
Only 14-time winners Real Madrid also made it through to the last 16 without dropping a single point, and a 3-2 beating of Red Star on the final matchday in Group G extended the holders' winning run in the Champions League to eight games, the longest streak for an English side in the tournament's history.
Since following up that nervy success with a 2-2 draw at home to Crystal Palace, Man City have reverted to type with a terrific 10-game winning run across all tournaments, briefly sitting atop their Premier League perch on Saturday thanks to Erling Haaland's brace in a 2-0 beating of Everton.
Not since Guardiola's maiden campaign in 2016-17 have Man City packed their bags in the last 16 of the Champions League, and the Citizens crushed Copenhagen 5-0 at the Etihad during the 2022-23 group stage, although their only two visits to the Danish champions' turf have both ended in a share of the spoils.
After scoring the goal which sent Copenhagen through to the knockout phase at the expense of Galatasaray, Copenhagen midfielder Lerager was banished from the field for two bookable offences, ruling the 30-year-old out of Tuesday's first leg through suspension.
Rasmus Falk, Viktor Claesson and 19-year-old Oscar Hojlund - brother of Man United's Rasmus Hojlund - are all options to deputise for Lerager, who joins the injured Davit Khocholava (knee) and Theo Sander (knee) on the sidelines, while Birger Meling's muscular injury renders the left-back doubtful too.
Ex-Arsenal goalkeeper Alex Runarsson and Nottingham Forest loanee Scott McKenna have both made Copenhagen's knockout squad since their January arrivals, and a few eyes will be on much-coveted 18-year-old Roony Bardghji, scorer of his side's fourth in their seven-goal spectacular with Man United.
While Copenhagen have a handful of concerns to manage, Man City travel to the Danish capital without Josko Gvardiol, Sergio Gomez or Mateo Kovacic, although it is unclear whether they have sustained injuries or have simply been overlooked.
Ruben Dias is one booking away from a European ban, but the Portuguese's tightrope-walking will have little bearing on Guardiola's selection, and after the quintessential 'Pep roulette' came into play against Everton, a few changes ought to be in store for the champions in midweek.
Kyle Walker, Bernardo Silva and Kevin De Bruyne should all return to the fray after entering Saturday's game as substitutes, while a revitalised Haaland leads the charge after making it 50 goals frm 50 Premier League starts, unsurprisingly a new competition record.
Copenhagen possible starting lineup:
Grabara; Ankersen, Diks, Vavro, Jelert; Goncalves, Falk, Claesson; Elyounoussi, Bardghji, Achouri
Manchester City possible starting lineup:
Ederson; Walker, Dias, Stones, Ake; Silva, Rodri, De Bruyne; Doku, Haaland, Foden
We say: Copenhagen 0-2 Manchester City
Already trying and failing twice to get the better of Copenhagen on their own territory, the third time should be the charm for a near fully-fit Man City on Tuesday, especially with the hosts losing such an influential figure in Lerager.
The Parken atmosphere is an intimidating one for any visiting team to emerge to, but with Guardiola's men enjoying their customary winter-to-spring surge, a first-leg advantage should be theirs to take back to the Etihad.
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