Next month's trip to Liverpool is a no-go for Kevin De Bruyne, while March's crunch derby with Manchester United could be a return date for Manchester City's star midfielder.
That is the predicament facing Pep Guardiola after he confirmed the Belgium international will be out for four to six weeks due to a hamstring injury sustained during the 2-0 midweek win over Aston Villa.
De Bruyne, the reigning PFA Players' Player of the Year, has been in typically sparkling form for City this term, scoring three times and providing 10 assists in the Premier League.
Guardiola's men are two points shy of league leaders United with a game in hand and into the last-16 of the Champions League.
Here, we look at the key games within a battle on all fronts where the EFL Cup finalists will be missing their talisman.
Cheltenham Town (A) - January 23
De Bruyne would probably have been rested for the weekend clash with League Two Cheltenham Town in any case, although the fifth round on February 10 also looks to be out of the question if City progress. In 16 appearances in the FA Cup, he has five goals and as many assists - claiming one of each in the 6-0 demolition of Watford in the 2019 final
West Brom (A) - January 26
City are back in Premier League action against Sam Allardyce's relegation-threatened Baggies next week. De Bruyne has two goals and three assists against the Baggies in the competition but could not manage a goal involvement as Ilkay Gundogan and Raheem Sterling failed to convert his late crosses during December's 1-1 draw at the Etihad Stadium. City have won nine games in a row across all competitions since that setback.
Sheff Utd (H) - January 30
Another relegation candidate follows, with bottom club Sheffield United facing a daunting trip to Manchester. De Bruyne created Sergio Aguero's opener before completing the scoring for a 2-0 win in this fixture last season.
Burnley (A) - February 3
Perhaps surprisingly, giving City's succession of recent 5-0 wins over Burnley, De Bruyne has never scored against Sean Dyche's men in the Premier League. He does have three assists, including the decisive passes for Riyad Mahrez and Benjamin Mendy to net during the most recent mauling last November.
Liverpool (A) - February 7
De Bruyne scored from the penalty spot as City beat the recently crowned champions 4-0 last July, although he missed uncharacteristically from 12 yards in this season's 1-1 draw at the Etihad Stadium. Even though none of his five Premier League assists against Liverpool have come at Anfield, he will be a huge miss when City chase a first win on the red side of Stanley Park since 2003.
Tottenham (H) - February 13
De Bruyne scored in each of his first three Premier League appearances against Spurs and set up both City goals as the sides shared a thrilling 2-2 draw at the Etihad last season. Jose Mourinho's men were the last team to inflict a defeat upon City, 17 games ago.
Arsenal (A) - February 21
No Premier League team has conceded more goals to De Bruyne than Arsenal's five. City's number 17 scored twice and dazzled throughout in a 3-0 win at Emirates Stadium last term.
Borussia Monchengladbach (A) - February 24
UEFA named De Bruyne their Midfielder of the Season following his performances on City's run to the quarter-finals in 2019-20. Despite his club's patchy record in Europe's top competition, the 29-year-old has seven goals and 15 assists in 37 Champions League appearances for the English side.
West Ham (H) - February 27
Rodri converted De Bruyne's corner before the man himself rounded off a 2-0 win over West Ham when the teams met on February 19 last year. It was the last time fans were allowed into the Etihad Stadium.
Manchester United (H) - March 6
This could be the biggest Manchester derby for almost a decade given the state of play at the top of the table and must surely be the comeback target for De Bruyne. He opened the scoring in a 2-1 Premier League win at Old Trafford in 2016, a strike that remains his only goal involvement in seven league games against United.
Juventus 0-1 Milan: Giroud decides top-four battle in Rossoneri's favour
Milan secured a top-four Serie A finish with a 1-0 win at Juventus as Olivier Giroud's header dealt a knockout blow to the Bianconeri's own hopes of Champions League qualification.
Still reeling from their 10-point deduction and Monday's miserable 4-1 defeat at Empoli, Juve required a win at Allianz Stadium to take the top-four battle to the season's final matchday.
However, the Bianconeri's lack of attacking thrust was on full display once again, with Giroud scoring the only goal of the game with an outstanding header as half-time approached on Sunday.
The Rossoneri were comfortable from there as they ensured Juve's chaotic season will end on another sour note, piling more pressure on embattled head coach Massimiliano Allegri.
Sandro Tonali headed Junior Messias' delivery over as Milan started brightly, but Juve soon improved, with Angel Di Maria failing to hook Moise Kean's cut-back home on the stretch.
More Bianconeri chances came and went as Federico Chiesa hammered over and Kean worked Mike Maignan from distance, but Juve found themselves behind five minutes before half-time.
Davide Calabria's hanging cross from the right was met with a textbook header from Giroud, who planted the ball beyond Wojciech Szczesny's despairing dive.
Adrien Rabiot forced a comfortable save from Maignan as Juve toiled after the restart, failing to make any attacking headway without injured striker Dusan Vlahovic.
Szczesny stuck out a leg to deny Alexis Saelemaekers and Rafael Leao fired over on the break, while Danilo had a close-range effort blocked in a goalmouth scramble as Juve's bid for Champions League football ended with a whimper.
What does it mean? Milan profit from Juve woes
When Juventus' 10-point deduction was confirmed earlier this week, Milan were the chief beneficiary after being propelled into the top four.
Stefano Pioli's men were determined not to let that advantage slip here, the Rossoneri weathering the Juve storm midway through the first half and deserving the three points after Giroud's goal.
Milan thus completed just their third Serie A double over Juventus in the last 50 years, also doing so in the 1990-91 and 2009-10 campaigns.
Giroud the man of the moment
Giroud has so often been the man for the big occasion for both club and country, and he gave Szczesny no chance with a firm header just as Juventus looked to be in the ascendency.
The 36-year-old striker has now scored 12 times in Serie A this season, his best return in one of Europe's top five leagues since he hit as many Premier League goals for Arsenal in the 2016-17 campaign.
Fatal blow for Allegri?
Allegri has faced stern criticism for most of the campaign, and the pressure may just become intolerable now they will finish outside of Italy's top four for the first time since 2010-11 (when they finished seventh).
Having also fallen short in the Europa League semi-finals, the Bianconeri have suffered three successive defeats for the first time since doing so in 2011 under Luigi Delneri.
What's next?
Milan wrap up their Serie A season against Verona next Sunday, while Juventus will be playing for a Europa League place when they visit Udinese on the same day.
Injury concerns for Kevin De Bruyne and Jack Grealish ahead of FA Cup final
Pep Guardiola admits he does not know if Kevin De Bruyne and Jack Grealish will be fit for next weekend’s FA Cup final.
Manchester City’s attacking duo, and defender Ruben Dias, missed the
1-0 final-day defeat at Brentford through injury.
The champions, who face Manchester United at Wembley on Saturday as they bid to complete the second leg of an historic Treble, were consigned to defeat by Ethan Pinnock’s late goal.
With De Bruyne and Grealish missing completely and left on the bench, it was a scratch City side and those established stars who did play, like Phil Foden and Riyad Mahrez, had little impact.
But Guardiola said: “Congratulations to Brentford for the victory. It’s difficult to faze them, how quick they play, how aggressive they are in all departments.
“I’m pretty sure we would have behaved a little bit different if we needed the points.
“I don’t have any complaints of how we behaved, I said to the players just now ‘you won the title, enjoy two days with your families and then we will prepare for the first final’.
“The guys who didn’t play who normally play were exhausted yesterday, mentally completely drained. They needed to rest to arrive with the right energy to face United.”
When asked if the players who missed out would be fit for Wembley, Guardiola said: “I don’t know right now. Hopefully.
“Ruben, Jack and Kevin couldn’t play. It is what it is. I think they will be ready but it’s hard to get ready in training. That’s why I had to see the players who played today.”
Pinnock’s 85th-minute strike made Brentford the only team to do the double over City this season, and only the fifth since Guardiola took over in 2016.
The Spaniard added: “They are the best team by far at set-pieces, they are exceptional. What Thomas Frank has done for years is amazing and the unity of his squad is there for all to see.
“Hopefully we can do better and beat them like we did last season, so we have a target for next season already.”
The Bees still needed a double save from goalkeeper David Raya to deny Cole Palmer at the death to end another impressive season on a high.
They had a slim chance to qualify for the Europa Conference League, and although victories for Tottenham and Aston Villa ultimately scuppered that dream, they finished a creditable ninth.
“Of course beating them twice means something, it means even more for the fans, they like that narrative and hopefully City win the Treble,” said Frank.
“Ending ninth in the Premier League, getting 59 points – and maybe deserve to have even more – it’s incredible the journey we have been on.
“What advice would I give United and Inter Milan? Well, I think we top performed in those two games.
“They are the best offensive team in then world so you need to defend very well and we did, and we were very brave throughout the game. I loved that from my players.”
Barcelona 3-0 Mallorca: Fabulous Fati fires up Camp Nou farewell
Ansu Fati's fabulous first-half double fired LaLiga champions Barcelona to victory in their Camp Nou farewell with a 3-0 win over Real Mallorca.
The Blaugrana signed off from their famous stadium in style, with Gavi also netting in a comfortable win over their 10-men visitors on Sunday.
In what was their final home game at their iconic ground before a temporary move to facilitate a lengthy renovation, Xavi's side ensured they bade it a fitting goodbye.
After losses against Real Sociedad and Real Valladolid, it also marked an impressive return to form.
Barca needed less than a minute to carve open their visitors, with Fati tucking away a Gavi cutback following a neat Robert Lewandowski ball into the box.
Matters soon worsened for Mallorca, when Amath Ndiaye saw his yellow card upgraded to a red by VAR for a shocking foul on Alejandro Balde.
Fati doubled his tally after that with a close-range rocket off Lewandowski's deft one-touch set-up, and Barca never looked like losing control from there on out.
Mallorca dug their heels in, but even then remained under siege, with Jules Kounde hitting the bar with a header shortly after the restart.
Lewandowski crashed a free-kick against the woodwork too, but Barca finally found their third when Gavi lashed a low finish beyond Dominik Greif.
There were standing ovations for Jordi Alba and Sergio Busquets on their final home appearances, with the Camp Nou crowd rising to salute the club legends.
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