Manchester City did the easy part by having manager Pep Guardiola sign a two-year contract extension at the Etihad Stadium earlier this month. However, the real challenge will be resolving the futures of the 16 first-team players whose own contracts are due to expire between now and the end of Guardiola's new deal in 2027.

Erling Haaland, Kevin De Bruyne, Jack Grealish, Bernardo Silva, Phil Foden and Ballon d'Or winner Rodri are all in that bracket, and there is a growing backlog of players at the club who will face significant decisions about their futures in the months ahead.

There are some pretty big numbers hovering over City right now. The 115 charges of breaching the Premier League's financial regulations, the eight-point gap between themselves and league leaders Liverpool ahead of Sunday's clash at Anfield, the five-game losing streak ended only by Tuesday's 3-3 draw with Feyenoord in the Champions League -- a shocking result in which they conceded three times in the final 15 minutes -- and the 4-0 defeat against Tottenham Hotspur last Saturday, which was City's heaviest on home turf since 2003. But the issue of the 16 contracts is one ticking away in the background while the focus remains fixed on the team's struggles on the pitch and the club's battle against the Premier League off it. City deny all charges and a hearing at the International Dispute Resolution Centre has been in session since September.

Events off the pitch at the London hearing are now intertwined with City's uncharacteristic loss of form in all competitions, however, in terms of what happens next with those players who will expect clarity over their futures. Uncertainty over the outcome of the Premier League hearing and what a defeat could mean for City -- the club could be fined, hit by a huge points deduction or even expelled from the league itself, although that is a highly unlikely scenario -- means that players and their representatives will be reluctant to commit to a new contract until the club's future is known.

There is already evidence of players being cautious over negotiating new deals due to the looming charges. Since the charges were announced in February of 2023 -- aside from back-up goalkeepers Stefan Ortega and Scott Carson, who both signed extensions this summer -- no first-team player has signed a new deal at City since Kyle Walker signed a two-year extension in September last year.

As Liverpool have discovered this season, having allowed Mohamed Salah, Virgil van Dijk and Trent Alexander-Arnold to enter the final year of their contracts at Anfield, any failure to address a key player's contract at least 18 months before it is due to expire leads to the prospect of the player leaving for nothing at the end of their existing deal. As it stands, City are approaching a critical period for their "class of 2027."

Haaland, Grealish, Rodri, Foden, Rúben Dias, Manuel Akanji, Mateo Kovacic and Nathan Aké are all out of contract in 2027. Some will be deemed to be expendable by the club and moved on before that, but Haaland, Foden, Rodri and Dias would seem to be priority extensions and therefore signed up by the end of 2025. However, if City's legal battle with the Premier League runs until late May -- something that's anticipated due to both parties being able to appeal the initial verdict, which is expected in January -- it is inconceivable that any of those players will commit to a new deal before that verdict is known.

Yet there are other players to address before 2027. Ilkay Gündogan and De Bruyne are both out of contract at the end of this season. At 34 and 33 respectively, both midfielders could leave next summer, with De Bruyne saying this week that his future is still to be decided. "Talks will come," he said. "If no talks come it will be my last year."

Beyond next summer, there are six players -- Silva, Walker, Ortega, Ederson, John Stones and James McAtee -- who will be out of contract in June 2026, meaning talks must quickly progress with those that City want to keep. Aside from the 22-year-old McAtee, all of those players are aged 30 or older so if they are to be moved on, City must replace them with new signings. When you add to the equation the change of key personnel at City, with long-serving director of football Txiki Begiristain to be replaced by Sporting CP's Hugo Viana next summer, it points to a complex period for the club with so many contracts to resolve in a short timeframe.

Guardiola's contract extension at least eradicated the crucial question of the manager's commitment to the club. With the 53-year-old's previous deal set to expire next summer, any ongoing failure to sign a new contract would have made it virtually impossible to offer players -- both existing squad members and potential targets -- a vision of a bright future at City.

That said, persuading a manager to sign a new contract is not the same as doing so with a player. If a player signs a new deal, a rival club would have to pay a transfer fee to get him out of that contract should he want to move on, and few clubs have the financial power to prise a star player from City. Once a player signs a long-term deal with City, they would be committed to that for the length of the contract.

At the other end, managers come and go. In August 2015, Manuel Pellegrini signed a two-year contract extension as City manager to commit him to the club until 2017, despite the wheels already being in motion for Guardiola take charge in 2016. Yet securing Pellegrini to a new contract was good message management by City in that it silenced speculation over his future and enabled the club to offer clarity and certainty to the players.

Only time will tell if Guardiola's new contract runs its course or if whether it merely serves the same purpose as Pellegrini's, but the true test of City's stability and the club's confidence in its future is not centred on thrashing out a new deal with Guardiola. The test is all about being able to keep their players by persuading them to follow Guardiola, but City are already battling against the clock on that.