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

We’ve all enjoyed the semi-regular late winter sight of a Premier League team in semi-realistic pursuit of the quadruple before it all inevitably collapses under the sheer fixture-congesting weight of it all.

But 2025/26 is already spoiling us by having not one but two teams reaching the end of February with everything still up for grabs, and a fairly decent prospect of that remaining the case right up until one knocks the other out of contention in the Carabao Cup final.

So here, then, are the key upcoming dates in Arsenal and Manchester City’s concurrent and inevitably doomed to humiliating failure bids to join the ranks of the Quad Gods.

February 22: Tottenham v Arsenal

One of the biggest games of the season, with massive repercussions at both ends of the table, and it marvellously arrives at a time when both teams are beyond rattled.

A bewildered Spurs fanbase, having spent two months being told by the media to stop being impatient and entitled and cruel to lovely Thomas Frank even though he was guiding them listlessly into a relegation fight, were left to watch in some wonder the sight of Arsenal having a complete meltdown in the wake of drawing one game in a title race they are still winning.

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

Which brings us to the Tottenham Hotspur Stadium.

Arsenal being very obviously very rattled once again and now coming up against a Tottenham team with the potential for new-manager bouncery under Igor Tudor has provided almost, if anything for me, Clive, too much narrative and an unexpected air of uncertainty to an already formbook-defenestrating fixture that nevertheless remains a clash between a very sh*t team and a very good team that really, really ought to go only one way.

February 27: Champions League knockout draw

We already know, of course, that both Arsenal and Manchester City are safely into the last 16 after finishing first and eighth in the league phase.

But the draw for the knockout bracket on Friday will give us plenty of clues about how the quad-hunting narrative may play out over the weeks and months ahead.

Most obviously, we’ll know when precisely Arsenal and Man City might meet directly in that competition. There are only two possible meeting points: quarter-final, or final. Either way, that means it comes after the Carabao Cup final has exposed one of this pair’s quadruple fraudulence.

Based on first-leg results from the punishment round, Arsenal will likely face German opposition – either Borussia Dortmund or Bayer Leverkusen. City might be more invested in the specifics of their opponents, because it looks like it’s going to be Bodo/Glimt… or Real Madrid.

March 1: Arsenal v Chelsea

Apart from a very obvious and potentially decisive trip north in mid-April, Arsenal really don’t have too taxing a run-in. Of the four teams in apparent contention for the (probably) three remaining Champions League places, Arsenal have already played Villa, Liverpool and Man United twice.

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

Next weekend’s visit of Chelsea is thus the only remaining Arsenal league game apart from that trip to Man City where anything other than routine victory will be expected. Which we’re sure will work out just fine for Mikel and the lads.

March 7: FA Cup fifth round

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

Although, to be fair, only one of our brave quad-chasers is playing a team they’ve already beaten three times in 2026 and it ain’t the so-called Premier League so-called leaders.

March 10-18: Champions League last 16

Arsenal will be warm favourites to sort out either of their likely last-16 foes, with Leverkusen currently down in sixth place in the Bundesliga and Borussia Dortmund having already managed to lose to actual Tottenham this season.

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

March 22: Carabao Cup final

The rare beauty of having not one but two quad-hunters at this late stage is that you’re looking at the prospect of a direct play-off between the two in the Carabao, where the death of one team’s hopes and the enhancement of the other’s will be given far, far more weight in the post-match fallout than someone or other winning a Carabao that sits right at the bottom of both teams’ priority list.

Fair to say Man City are by far the most at risk of being out of quad contention before we get this far, with a far tougher FA Cup assignment to negotiate and the ticklish prospect of a bit of Real Madrid to deal with in the Champions League.

They are also still playing catch-up – albeit quite effectively – in the league and are thus the only team that could really have f*cked themselves out of Premier League contention over the next month despite Arsenal’s current efforts at transporting their heads directly to Mars.

So it’s mainly on City to make sure we get what we all want: an actual major final that is viewed entirely through the prism of what it all means for events yet to come.

Otherwise there’s a real risk that it just becomes ‘Arsenal end their trophy drought’ and that won’t do.

April 4-5: FA Cup quarter-finals

Bonus points if it’s Arsenal and City going directly at each other 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 it’s Arsenal and City going directly at each other 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 this moves from 3pm on Saturday April 11 to a TV slot, but we won’t know for another couple of weeks which one, so we’re having to fudge the date a bit for now. But it’s a mighty significant game – especially given what takes place the weekend after.

We all love a fixture-list quirk, and a notable one for this season’s title run-in is that the two big standout remaining fixtures where things might go wrong before the final day for both City and Arsenal are against each other and Chelsea.

April 19: Manchester City v Arsenal

It’s still currently officially scheduled for Saturday April 18 but we’re going to go ahead and assume this one makes its way directly to the Super Sunday headline slot.

Because whatever has happened to these teams’ quadruple chances by this point, it’s almost impossible now to imagine this game not having a significant bearing on at least the title race.

There are still five full rounds of Barclays to follow, so it surely cannot be officially and finally decisive but it seems absolutely certain that the result of this one will matter.

And at this point, still almost two months removed, the range of just how much it matters remains gloriously wide open. We could just about be in ‘all-but’ territory for the ‘champions-elect’ winner if things have gone hilariously for one or other team in the meantime. Certainly it could be there for someone to ‘take a giant stride toward’ the title and perhaps even to ‘have one hand on the trophy’.

Yet there’s plenty of scope for someone to ‘breathe new life’ into the title race, or perhaps ‘kickstart’ their challenge, or get it ‘back on track’. At this point we don’t even know what the accepted consensus answer to the question ‘Which side will be happier with a point, do you think?’ might be.

It’s all just tremendously exciting.

Date TBC: Man City v Crystal Palace

It might not be the end of the fixture shuffling required, but for now this is the conspicuous unconfirmed lurker in the run-in. This is the fixture that fell by the wayside on Carabao Cup final weekend, with Palace’s Europa Conference punishment round commitments meaning, unlike Wolves v Arsenal, it could not be moved forward to a convenient empty midweek.

The earliest that now looks possible is the week commencing April 20, so that’s where we’ve shoved it in here for now.

And that would be a saucy little spot for it to turn up as well, especially if City have beaten Arsenal the weekend before and with it the potential of a six-point swing. Of course, the reverse is equally true if Arsenal get a result at the Etihad and then City fumble a fixture everyone will have spent the previous two months assuming they would win.

But wherever it lands it’s going to matter, offering as it does the chance for City to snag three points to which Arsenal have no answer.

April 25-26: FA Cup semi-finals

It’s around about this point that you start to realise why nobody ever actually manages to do this. It just looks like an exhausting amount of hard work.

April 29-May 6: Champions League semi-finals

Were the Champions League knockout bracket fully seeded rather than just pair-seeded, the league phase outcome would have Arsenal seeded to meet Spurs in the last four. What a world. Could still happen, of course. If 2026 has taught us nothing else, it’s to rule nothing out.

May 16: FA Cup final

FUN FACT: Pep Guardiola has only ever bothered to win the FA Cup as part of a treble; domestic in 2018/19, continental in 2022/23. Maybe this time it’ll be for the quad?

May 24: Premier League final day

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

Possible, of course, that Villa still have work of their own to do in the hunt for Champions League qualification, while it’s still not entirely outlandish to suggest Palace – in what is slated to be Oliver Glasner’s final game in charge – might still have a bit of relegation-avoiding to take care of.

All four teams with something tangible to play for would be a proper final-day treat and we are now greedily demanding just that. Create some more peril.

It often takes a circuitous route to get there, but these days it does feel like whenever we get a final-day decider it just ends up finishing as you were. For some reason, we feel it deep in our bones that this season will be different if it comes down to it. We fear for whoever’s leading heading into the final day, we really do.

May 30: Champions League final

If either City or Arsenal are still in with a chance at this point, fair play. It’ll be great fun for the rest of us to gamely try and make a season featuring a domestic treble into a disappointment and missed opportunity should they fall at this final and most difficult hurdle. We’re sure we can pull it off.