Key dates as Arsenal and Manchester City go in search of the elusive quadruple

We’ve all enjoyed the semi-regular late-winter spectacle of a Premier League team in semi-realistic pursuit of the quadruple before everything inevitably collapses under the cumbersome weight of it all.

But 2025/26 already spoils us by having not one but two teams reaching the end of February with everything still up for grabs, and a pretty decent prospect of that remaining the case until one eliminates the other in the Carabao Cup final.

So here are the main upcoming dates for Arsenal and Manchester City’s simultaneous matches. inevitably doomed to humiliating failure offers to join the ranks of the Quad Gods.

February 22: Tottenham v Arsenal

One of the biggest matches of the season, with massive repercussions at both ends of the tableand it comes wonderfully at a time when both teams are beyond shaken.

A baffled Spurs fan base, having spent two months being told by the media to stop being impatient, entitled and cruel towards the charming Thomas Frank even if he casually guided them into a relegation fightwere left staring in wonder at the sight of Arsenal completely collapse after draw in a title race, they always win.

You can understand it, though: you just won’t catch seasoned title winners Man City inexplicably taking a comfortable 2-0 lead in a wild second half at the home of beleaguered relegation stragglers. Don’t try to imagine this happening, it has never happened and never will.

Which brings us to the Tottenham Hotspur Stadium.

With Arsenal obviously very rattled once again and now coming up against a Tottenham side with the bounce-back potential of a new manager under Igor Tudor, it provided almost, if anything for me, Clive, too much narrative and an unexpected air of uncertainty to an already defenestrating match. It still remains a clash between a very bad team and a very good team which really, really should only go one way..

February 27: draw for the knockout stages of the Champions League

Of course, we already know that Arsenal and Manchester City are both safe in the last 16 after finishing first and eighth in the championship stage.

But Friday’s Round of 16 draw will give us plenty of clues as to how the quad chase narrative could play out in the weeks and months to come.

Obviously, we will know exactly when Arsenal and Man City could meet directly in this competition. There are only two possible meeting points: quarter-final or final. Either way, that means it comes after the Carabao Cup final exposed one of this pair’s quadruple cheats.

Based on the results of the first leg of the penalty round, Arsenal will likely face a German opponent – ​​either Borussia Dortmund or Bayer Leverkusen. City might be more invested in the specifics of their opponents, as it looks like it will be Bodo/Glimt… or Real Madrid.

March 1: Arsenal v Chelsea

Aside from a very obvious and potentially decisive move north in mid-April, Arsenal really don’t have a game that’s too taxing. Of the four teams seemingly in contention for the (probably) three remaining Champions League places, Arsenal have already faced Villa, Liverpool and Man United twice.

There really is an awful lot of pish during their run-in, ending with three games against teams currently in the bottom seven.

Next weekend’s visit to Chelsea is therefore Arsenal’s only remaining league game, apart from this trip to Man City where something other than a routine victory is expected. Which we’re sure will work out great for Mikel and the guys.

March 7: FA Cup fifth round

We mean no disrespect when we say Man City (at Newcastle) face a tougher test here than Arsenal (at Mansfield).

Although, to be fair, only one of our plucky quad-chasers is facing a team they’ve already beaten three times in 2026 and they’re not the so-called leaders of the Premier League.

March 10-18: Champions League round of 16

Arsenal will be hot favorites to eliminate either of their likely round of 16 opponents, with Leverkusen currently in sixth place in the Bundesliga and Borussia Dortmund have already managed to lose to Real Tottenham this season.

City’s chances are less clear until the draw is made. Sure, they lost pretty badly to Bodo in the group stage, but you’d still have a knockout match against the Norwegians to deal with Real Madrid again.

March 22: Carabao Cup final

The rare beauty of having not one but two quad chasers at this late stage is that you’re looking at the prospect of a straight play-off between the two in the Carabao, where the death of one team’s hopes and the improvement of the other’s will carry far more weight in the post-match fallout than someone or another winning a Carabao which is way down on both teams’ priority list.

It’s fair to say that Man City are by far the most at risk of being out of the competition before they get that far, with a much tougher mission to negotiate in the FA Cup and the tricky prospect of a bit of Real Madrid to face in the Champions League.

They are also still playing catch-up – albeit quite effectively – in the league and are therefore the only team that could really have crashed out of Premier League competition over the next month despite Arsenal’s current efforts to transport their heads straight to Mars.

So the onus is primarily on City to ensure we get what we all want: a truly major final that is viewed entirely through the prism of what it all means for events to come.

Otherwise there is a real risk that this will simply become ‘Arsenal end their trophy drought’ and that won’t be enough.

April 4-5: FA Cup quarter-finals

Bonus points if Arsenal and City face each other directly again. Double bonus points for anyone who keeps a straight face while calling success here “revenge for Carabao Cup disappointment”.

April 7-15: Champions League quarter-finals

Bonus points if Arsenal and City face each other directly again. Triple bonus points for anyone who keeps a straight face while calling success here “revenge for Carabao Cup disappointment”.

April 11-12: Chelsea v Man City

We’re pretty sure it will move from 3pm on Saturday April 11th to a TV slot, but we won’t know for a few weeks which one, so we have to fudge the date a bit for now. But it’s an extremely important match, especially considering what unfolds the following weekend.

We all love the quirks of the fixture list, and one of the notable quirks of this season’s title race is that the two remaining big matches where things could go wrong before the final day for City and Arsenal are against each other and against Chelsea.

April 19: Manchester City v Arsenal

It’s still officially scheduled for Saturday, April 18, but we’re going to go ahead and assume this one is heading straight for the Super Sunday title.

Because whatever happened to these teams’ quadruple chances at this stage, it is almost impossible now to imagine that this match would not have a significant influence at least on the title race.

There are still five full rounds of Barclays to follow, so surely this can’t be officially and definitively decisive, but it seems absolutely certain that the outcome of this one will matter.

And at this point, after almost two months of delay, the scope of significance remains gloriously wide open. We could be in “anything but” territory for the winner of “Champions Chosen” if things have gone hilariously wrong for either team in the meantime. He could definitely be there for someone to “take a giant step towards” the title and maybe even “get a hand on the trophy”.

Still, there are plenty of opportunities for someone to “breathe new life” into the title race, or perhaps “revive” their challenge, or “get them back on track.” At this point, we don’t even know what the accepted consensus answer to the question “Which side do you think will be most satisfied with a point?” » could be.

This is all extremely exciting.

Date to be confirmed: Man City v Crystal Palace

This may not be the end of the required device rework, but for now, it’s the visible and unconfirmed lurker in the lurker. This is the game that was abandoned last weekend’s Carabao Cup, with Palace’s Europa Conference punishment round commitments meaning that, unlike Wolves against Arsenal, it could not be brought forward to a convenient empty midweek.

The earliest that now seems possible is the week starting April 20, so that’s where we’ve inserted it here for now.

And it would also be a cheeky little place for him to appear, especially if City had beaten Arsenal the previous weekend and with it the potential for a six-point swing. Of course, the opposite is also true if Arsenal get a result at the Etihad and City miss a game that everyone will have spent the previous two months thinking they would win.

But wherever he lands will matter, giving City the chance to take three points that Arsenal have no answer for.

April 25-26: FA Cup semi-finals

This is about the point where you start to understand why no one ever succeeds. This sounds like an exhausting amount of work.

April 29-May 6: Champions League semi-finals

If the Champions League round of 16 were fully seeded rather than just pairwise, the result of the league stage would put Arsenal top seed to face Spurs in the last four. What a world. It could still happen, of course. If 2026 has taught us nothing else, it is to exclude nothing.

May 16: FA Cup final

FUN FACT: Pep Guardiola never bothered to win the FA Cup as part of a treble; national in 2018/19, continental in 2022/23. Maybe this time it will be for the quad?

May 24: last day of the Premier League

Man City host Aston Villa and Arsenal travel to Crystal Palace on the final day. If the title race is still on at this point, it’s a really fun final day.

It’s of course possible that Villa still have some work to do in the race for Champions League qualification, while it’s still not entirely outlandish to suggest that Palace – in what is expected to be Oliver Glasner’s final game in charge – might still have a bit of relegation to avoid.

All four teams having something tangible to play for would be a real treat for the final day and that’s exactly what we’re now hungrily demanding. Create even more peril.

It often takes a circuitous route to get there, but these days it seems like every time we have a final day decider, it ends up ending like you did. For some reason, we feel deep in our bones that this season will be different in the end. We fear for whoever leads before the last day, we truly fear him.

May 30: Champions League final

If City or Arsenal still have a chance at this stage, fair play. It will be great fun for the rest of us to try to make a season marked by a domestic treble a disappointment and a missed opportunity if they fall at that final, hardest hurdle. We are sure we can achieve this.