Will they win one, two, three… or all four? Manchester City are about to resume their bid for an unprecedented quadruple and one of the things on their side is that - unlike most other teams - they have been here before.

No club has ever landed the Premier League, Champions League, FA Cup and League Cup all in the same season, but this is City's fourth serious attempt at a clean sweep in the past seven years.

That experience of chasing multiple major trophies in the final few weeks of the season should help them this time, as much for what went wrong previously as what they got right - and one of the lessons learned should have been that slip-ups can happen anywhere.
Beware of banana skins
Man City's route to winning each knockout competition in 2020-21
Competition QF SF Final
Carabao Cup Tottenham
FA Cup Chelsea Leicester/Southampton
Champions League Borussia Dortmund Bayern Munich/PSG Real Madrid/Liverpool/Porto/Chelsea

Right now, on paper, a potential Champions League semi-final showdown with Bayern Munich or Paris St-Germain probably looks like the biggest obstacle to what would be the greatest achievement in English club football's 133-year history.

City should beware of banana skins, however. They have previously appeared in some unlikely places - Wigan (twice) and Tottenham were the teams who stopped their charge on four fronts in 2014, 2018 and 2019.
The three times Man City have come closest to winning the quadruple (by date*)
Rank/Season Premier League FA Cup League Cup Champions League Bid over
1. 2018-19 Winners Winners Winners QF 17 Apr
2. 2013-14 Winners QF Winners L16 9 Mar
3. 2017-18 Winners 5R Winners QF 19 Feb

*Not including the delayed 2019-20 season

The best news for City is probably that they don't have to play Wigan again this time, but you can still see why Pep Guardiola, who was also in charge for both of those previous two campaigns, has been at pains recently to point out that his side have not won anything yet.

That in itself is an anomaly - the coronavirus pandemic is the only reason we are talking about a quadruple now, with City's trophy cabinet still not stocked up since the start of spring.
Manchester City celebrate winning the 2020 Carabao Cup - they have won the competition in each of the past three seasons and in four of the past five campaigns

The Carabao Cup would usually be done and dusted already, of course, but this year's final was rescheduled from its traditional slot in February in the hope fans would be able to attend.

City will face Spurs - yes, them again - at Wembley at the end of this month instead, hoping to belatedly bag their first trophy.
What is the closest anyone else has come?
The three times other English clubs have come closest to winning the quadruple (by date)
Rank/season Team PL / Div 1 FA Cup League Cup CL / EC Bid over
1. 2006-07 Chelsea 2nd Winners Winners SF 1 May
2. 2008-09 Man Utd Winners SF Winners Final 19 April
3. 1960-61 Burnley 4th SF SF QF 15 Mar

PL = Premier League, CL = Champions League, EC = European Cup

Arriving at the start of April with your hopes alive in all four major competitions is no mean achievement, though, whatever the circumstances.

English teams have had the chance of a quadruple since the League Cup was established in 1960-61 but, from a total of 117 attempts from 15 different clubs over the past 60 years, there have only been four other occasions when teams have got this far, date-wise, before.

They were Chelsea in 2007, Manchester United in 2009 and City in 2019 and 2020, although last summer was a little different. Guardiola's side technically had hope until Liverpool wrapped up the Premier League title in late June once the season had resumed after the coronavirus outbreak halted it in March.

Chelsea's attempt, the best so far under any normal schedule, lasted until 1 May, and a defeat by Liverpool in the Champions League semi-finals. Two years later, United fell to Everton with a penalty shootout defeat in the FA Cup semi-finals on 19 April.

That United team got to within three wins of all four major trophies, also losing to Barcelona in the Champions League final, and had to settle for 'only' two in the end.
The 15 English teams who have tried for a quadruple - and how far they got*
rank/club Attempts Best attempt? Bid ended?
1. Chelsea 15 2006-07 1 May
2. Man Utd 23 2008-09 19 Apr
3. Man City* 11 2018-19 17 Apr
4. Burnley 1 1960-61 15 Mar
5. Arsenal 21 2010-11 27 Feb
6. Nott'm Forest 3 1978-79 26 Feb
7. Liverpool 23 1982-83 20 Feb
8. Tottenham 5 2018-19 24 Jan
9. Newcastle 3 1997-98 10 Dec
10. Leeds 4 1992-93 13 Nov
11. Aston Villa 2 1981-82 19 Jan
12. Blackburn 1 1995-96 29 Nov
13. Derby 2 1972-73 9 Oct
14. Leicester 1 2016-17 20 Sep
15. Everton 1 2005-06 24 Aug
*Does not include delayed 2019-20 season
When Burnley almost went the distance

Before the Premier League and Champions League era began in 1992, Burnley went closest, in 1960-61 - the very first season four trophies were up for grabs in England - when they got as far as 15 March before losing to Hamburg in the quarter-finals of the European Cup.

Back then, quadruple opportunities were far more limited - the European Cup was restricted to just the league champions or holders and, for eight out of 10 seasons between 1961 and 1971, the clubs who qualified did not enter the League Cup.

There was no chance of completing it between 1985 and 1991 either, as English clubs were barred from Europe for five years, and league champions Liverpool served an extra year's suspension in 1990-91.

Some teams still had several early chances, though - notably the Liverpool side of the late 1970s and early 1980s, who had nine successive seasons in the European Cup between 1976-77 and 1984-85.

Their best effort at a clean sweep saw them complete a treble of the league title, European Cup and League Cup in 1983-84, but they went out of the FA Cup to second-tier Brighton on 29 January.

Out of a total of 23 attempts - the joint-most with Manchester United, who were denied a try in 1999-2000 when they did not take part in the FA Cup - the furthest the Merseysiders have come in terms of the date their quadruple bid ended was 1982-83, when they got as far as 20 February.
The three times Liverpool came closest to the quadruple (by date)
Rank/season Div 1 FA Cup League Cup European Cup Bid over
1.1982-83 Winners 5R Winners QF 20 Feb
2.1981-82 Winners 5R Winners QF 13 Feb
3.1983-84 Winners 4R Winners Winners 29 Jan

Other great teams of the modern era also fell short. United's famous Treble of 1998-99 included the FA Cup, not League Cup - they went out of that competition to Tottenham in the quarter-finals, on 2 December.

Arsenal's legendary 'Invincibles' went the entire league campaign undefeated in 2003-04, but that was the only silverware they secured that season and their quadruple hopes were ended on 3 February by Middlesbrough, who beat them 3-1 on aggregate in the League Cup semi-finals.
Manchester United's Treble-winning side celebrate their Champions League triumph in 1998-99

City's own 'Centurions' - the Guardiola side that broke the 100-point mark and set an all-time English top-flight record for most points in a single campaign in 2017-18 - had their bid ended by Wigan Athletic, of League One, in the FA Cup on 19 February.

A year later, in 2019, City became the first English men's team to do a domestic treble, but lost to Spurs in Europe on 17 April - date-wise, in a regular season, the third-best effort yet.

There have also been teams that ended up completely empty-handed - a fate that could still befall City this year, however unlikely it seems.

The Chelsea side of 2007-08 are probably the best example of that. They finished runners-up in the league by two points, lost in the final of the Champions League and League Cup, and were knocked out of the FA Cup in the sixth round.

What City need to do - and what's different this time?

Realistically, no-one is still wondering whether City will win anything this season - the only question is how many trophies they will collect.

When they last got to April with their hopes of the quadruple alive, in 2019, their midfielder Kevin de Bruyne described winning all four as "nearly impossible".

But that was because City were in the midst of a title tussle with Liverpool that went to the final day and was mentally and physically draining every week - they had to win their last 14 league games of the season to hold off the Reds.

This time, Guardiola's side have breathing space at the top of the Premier League, thanks to a run of 17 wins from 18 league games. In that respect, some of the pressure is off.

While City have been relentless, their rivals have continued to drop points. If United or Leicester merely maintain their current points-per-game ratio, the most they will gather is 75 points - so two wins would deliver the title to City, not five.

The knockout cup competitions, by definition, will be far more difficult to negotiate. City are the bookmakers' favourites to win each one, including in Europe but, as Guardiola will surely remind his players, that has hardly helped them there much in the past.

Despite his two previous successes with Barcelona, Guardiola has a personal point to prove in the Champions League too - he has never gone beyond the quarter-finals in four attempts with City, has not won it since 2011, and one of the few ways to criticise his stellar managerial career is that he has not got his hands on that particular trophy without having Lionel Messi in his team to help.

This year seems a particularly good opportunity to put all of that right but Guardiola's mantra is to take one game at a time, so he will not be contemplating this year's final - in Istanbul on 29 May - for a little while yet.