Sergio Agüero becoming Manchester City's all-time top scorer was the highlight of the night in Naples, as his goal and others from Nicolás Otamendi, John Stones and Raheem Sterling secured a 4-2 victory over Napoli.
It was in no doubt that it was the home side that dominated the early proceedings with Dries Mertens's disallowed goal before Lorenzo Insigne opened the scoring in the 21st minute, City managed to bring it back through Otamendi's header before the crossbar denied Stones giving them the lead just before the break.
The opening of the second period saw the momentum shift in City's favour as Stones helped them take the lead three minutes after the restart, however things were level once again through Jorginho's penalty but Agüero's historic strike and another from Sterling sealed the win and their knockout qualification.
Taking a deserved lead
Pep Guardiola knew going into this clash that his side just needed the win to see them into the knockout stages of the competition, but Maurizio Sarri's side who needed a win themselves were certainly not going to make it easy for the Citizens peppering them with chances in the early stages.
They thought that they finally made the breakthrough in the 19th minute as Mertens did well to get on the end of Jorginho's lofted ball, Mertens showed why he has become one of the most feared forwards on the continent as he slotted past the rushing Ederson but the flag went up for offside.
It wouldn't be long however until the current Serie A frontrunners managed to take their deserved lead, it was the goalscorer Insigne who stated the move as he played the one-two with Mertens. The Belgian span the ball excellently behind the bamboozled City defence before finishing above the rushing Ederson.
Managing to claw themselves back into the clash
Despite their form in recent weeks and months City had failed to make any chance of real merit inside the opening 30 minutes, but they were handed a valuable equaliser from an unlikely source.
It was steady build-up play from the English visitors as İlkay Gündoğan floated a great ball into the back post which found Otamendi who headed home his first Champions League goal at the perfect time.
They were a lick of paint away from taking an arguably undeserved lead with five minutes to play in the half, it was Gündoğan once again as his hooked effort failed to be reached by the goalscorer Otamendi. The Argentine's loss was Stones's gain as he was on the end of the deflection, but his header clattered Pepe Reina's crossbar.
Turning it all around
Whatever Guardiola said to his players at half-time in the Stadio San Paolo's dressing rooms clearly had an effect, as City turned the tie on its head by taking the lead early into the period.
It was nearly from the brilliance of Sterling as his trickery and determination took him past a handful of players before being one-on-one with Reina, but his effort was brilliantly blocked by Raúl Albiol.
From one of the subsequent corners City managed to take their lead, it was an excellent corner from Leroy Sané who found the rising head of Stones who looked to have been thwarted once again by the crossbar but the touch off the underside of the woodwork saw it creep over Reina's line.
Handed a way back in soft circumstances
The momentum of the game was swaying back and forth, and it favoured the Italians on the hour mark as they were handed a lifeline back into the clash.
The short corner didn't look any danger for the visitors as Albiol managed to nip in ahead of Sané, the young German looked to have kicked the Spaniard on the way through and despite looking on the soft side Felix Brych pointed to the spot.
Spot kicks at the Etihad Stadium proved to be a 50-50 success on the last matchday as Jorginho stepped up, but he made no mistake as casually sent Ederson the opposite direction.
Making history on the elite European stage
Nobody could have predicted the full-time result of the clash as it entered its final 20 minutes, but it would take a piece of history to separate the two sides.
City manage to break from the Napoli as the ball is played up to Sané who turns on the afterburners to storm towards goal, he is thwarted by the retreating defender but Agüero is on hand to pick it up and place it into the bottom corner.
Rounding it off in style
After the Argentine's piece of history City shut the game down and just tried to pass around their opponents as the clock ticked down, but one last punt upfield resulted in rounding off the first win for an English side in Naples.
It had been one of the more quiet nights for Kevin De Bruyne especially by his impeccably high standards but he ran at the non-existent Napoli defence as the seconds rolled by, he passed it out to Sterling on the far end of the area who took a touch before sweeping into Reina's far corner.