Despite throwing the kitchen sink - and a few billion pounds - in pursuit of winning the richest prize in soccer, all that Man City and PSG have got to show for their efforts are some runners-up medals.
The two financial giants will now go head-to-head in the group stage and both will see it as an opportunity to make a serious statement of intent.
When, where and how to watch
When: Tuesday, September 28, 8PM BST
Where: Parc des Princes
How to watch: BT Sport
Finishing strong before the international break is the aim of every club. However, that job has been made especially hard for Man City who follow up their win over Chelsea with games against PSG and Liverpool.
It's a tough couple of weeks for Pep Guardiola and his men. However, if there's anyone with the adequate tools and experience to cope, it's definitely the Spaniard.
The victory over Chelsea was huge. Not only did it end Guardiola's three match losing run against the Blues but it also gave Gabriel Jesus a moment to shine following his winning goal.
The Brazilian seemed marginalised when City tried to lure Harry Kane over to the Etihad. Perhaps that one goal could be a turning point for the striker's fortunes at the club.
The big news coming out of PSG is that Lionel Messi has returned to training. The Argentine has a terrific record against Guardiola in the Champions League having scored six goals in four games against teams led by the current City boss.
Despite that stat, it's fair to say that Messi has not set Paris alight in his first three appearances. That shouldn't come as a shock considering the 34-year-old has endured fitness and injury issues.
If he's fit though, he will undoubtedly be the man to watch. What's more, a fit Messi usually leads to goals.
With that in mind, both teams to score is our opening tip.
Last three meetings
Man City 2-0 PSG (Champions League - May 4, 2021)
Manchester City booked their place in the Champions League final with a two-goal victory over PSG.
Riyad Mahrez scored a brace as the visitors finished the match with 10 men following Angel Di Maria's sending off.
PSG 1-2 Man City (Champions League - April 28, 2021)
The first leg of last season's Champions League semi-final saw Guardiola's men secure a 2-1 win away in Paris.
Marquinhos opened the scoring for the hosts before two second-half efforts sealed a memorable win for the Manchester outfit.
Kevin De Bruyne and Mahrez were the goalscorers at Parc des Princes.
Man City 1-0 PSG (Champions League - April 12, 2016)
The two teams met in the quarter-finals of the 2015/16 Champions League campaign.
Following a 2-2 draw in the first leg, PSG needed to turn things around in order to avoid a defeat on away goals.
However, the Parisians failed to score as City secured a 1-0 win thanks to De Bruyne's 76th minute goal.
Last five head-to-heads
PSG wins: 0
Man City wins: 3
PSG goals: 3
Man City goals: 7
PSG hopeless against English opposition
As you can see above, PSG are winless against Manchester City. In fact, from their 25 games against English teams, the Parisians have only won on seven occasions.
Mauricio Pochettino will be expected to change that following one of the greatest transfer windows in soccer history.
In truth, the Argentine manager will be under pressure to win every competition under the sun.
Question is, can he handle the humongous egos in his team and mould together a cohesive soccer team? At the moment, early results would suggest he can.
While the performances may be lacking, it shouldn't be forgotten that PSG have won eight of their last nine games. During that time, they've also managed to score 23 goals.
Considering the Parisians have scored at least two goals in eight of their last nine matches, our second tip is to back them to bag over 1.5 goals at 11/8.
Man City's strange goal tendencies
It's hard to know what type of Manchester City we're going to get this Tuesday night.
Guardiola's men have been rather inconsistent when it comes to goals. The Cityzens either score once or score five plus goals - there's no middle ground.
Their 5-0 win over Arsenal, for instance, was followed by a 1-0 win over Leicester. A few days later they beat RB Leipzig 6-3 before drawing 0-0 with Southampton. Their next game saw the Sky Blues beat Wycombe 6-1 in the cup before winning 1-0 away against Chelsea.
Interestingly, eight from City's nine competitive games this season have ended with an odd number of goals.
With that in mind, we're backing that to happen again at an interesting price of 20/21.
Man City have scored a lot of goals this season despite their lack of a target man up front.
Goals can arrive from any area of Guardiola's team which makes betting in the goalscorer market all that more interesting when it comes to the Cityzens.
Ferran Torres and Gabriel Jesus currently lead the anytime scorer market but our recommendation is to back Jack Grealish instead.
The former Villa man marked his Champions League debut with a goal and an assist against RB Leipzig. At 13/5, he's worth a go to get among the goals once more.