Manchester City are out of the UEFA Champions League after losing 3-1 at AS Monaco tonight.
City took a 5-3 lead into the return bout at the Stade Louis II but fell agonisingly short on away goals after it ended 6-6 on aggregate.
Pep Guardiola has failed to get past the initial knockout phase of Europe's premier club competition for the first time in his managerial career as Leonardo Jardim's free-scoring French outfit advance to the final eight.
Monaco put City to the sword early and the opening goal came swiftly inside eight minutes when Bernardo Silva fired a low cross into the six-yard box from the left side which was poked home coolly by the impressive Kylian Mbappe.
City were being played off the park in the Principality and found themselves two goals down on the night, and behind on away goals, when Benjamin Mendy similarly sent a pinpoint ball in from the left which was met by a wonderful finish from Fabinho on 29 minutes.
The visitors were lucky not to go further behind before half-time, but Guardiola's charges came out breathing fire in the second half and looked menacing going forward, apart from the final attack.
The usually reliable Sergio Aguero had a golden opportunity to put City ahead overall on 62 minutes but failed to poke home a close-range volley after a blinding run from Leroy Sane down the left.
Moments later, David Silva picked out Aguero but the Argentine took a heavy first touch before firing into an onrushing Danijel Subasic.
But the goal City deserved finally came in the 71st minute when Raheem Sterling forced a save from Subasic which fell kindly for Sane who slotted home with consummate ease with an open net at his beck and call.
That had City back in the driver's seat but it only lasted a matter of six minutes as Tiemoue Bakayoko got on the end of a Thomas Lemar free-kick to superbly head home Monaco's third goal.
That was enough to see the Ligue 1 leaders over the line by virtue of the away-goal rule courtesy of the three they scored at the Etihad Stadium last month.
Monaco join Real Madrid, Barcelona, Atletico Madrid, Bayern Munich, Borussia Dortmund, Juventus and Leicester City in the quarter-final draw which takes place on Friday morning.
For Guardiola and City, they have only the FA Cup to play for with a semi-final against Arsenal on the horizon and a top-four spot in the Premier League so they can return to Europe next season.
2016/17 UEFA Champions League - Round of 16 2nd leg
AS Monaco (FRA): 3 (Kylian Mbappe 8', Fabinho 29', Tiemoue Bakayoko 77')
Manchester City (ENG): 1 (Leroy Sane 71')
*Monaco wins on away goals after 6-6 aggregate
Stade Louis II, Monaco, France - 15,700
Source: tribalfootball.com