Manchester City’s visit to Anfield is set to carry added significance, with the club returning to action following a verdict that found them guilty of 114 of 115 financial rule breach charges brought by the Premier League.
City continue to deny wrongdoing and are appealing the decision. However, the ruling has renewed debate about the club’s rise during a period in which they established themselves as one of English football’s dominant forces.
The timing of the verdict makes Sunday’s clash with Liverpool particularly intriguing. The two clubs have repeatedly battled for major honours over the past decade and beyond, while several high-profile transfers during that period saw City secure players who had also attracted interest from Anfield.
Financial Verdict Casts a Shadow Over Sunday’s Showdown
The Premier League accused City of using what it described as sham agreements to manipulate their financial accounts by approximately £900 million over nine seasons, from 2009 to 2018.
That period coincided with substantial success for the Manchester club, who won eight trophies during the timeframe under scrutiny. The verdict has therefore prompted renewed questions about how that era should be viewed, although City’s appeal means the legal process remains ongoing.
Liverpool were among City’s principal challengers during those years, with the sides producing several closely contested title races. City finished ahead of Liverpool in the Premier League in 2013-14, 2018-19 and 2021-22, while the Merseyside club secured the championship in 2019-20 and 2024-25.
Their rivalry has extended beyond the pitch, particularly in the transfer market, where City’s financial resources and growing ambitions helped them attract players who might otherwise have ended up at Liverpool.
Gareth Barry Chose City After Liverpool’s Failed Pursuit
Gareth Barry was one of the important early signings of Manchester City’s Abu Dhabi-backed era, but Liverpool had attempted to bring the midfielder to Anfield a year before his eventual move to the Etihad.
In the summer of 2008, Liverpool manager Rafa Benitez made several offers for Barry, with the bids reportedly reaching £15 million. Benitez wanted the Aston Villa captain to replace Xabi Alonso, whose relationship with the manager had become increasingly strained.
Villa refused to sell, leaving Barry frustrated. The situation deteriorated after he publicly criticised manager Martin O’Neill in an unauthorised interview, and he subsequently lost the captaincy.
Barry remained at Villa Park for another season before joining City in the summer of 2009 for approximately £12 million. His transfer coincided with Alonso’s departure from Liverpool to Real Madrid.
The move proved significant for both clubs. Barry became part of the City side that won the Premier League title in 2011-12, while Liverpool struggled to find the right midfield additions in the seasons that followed, signing players including Alberto Aquilani, Christian Poulsen, Jonjo Shelvey and Charlie Adam.
City’s ambition under Sheikh Mansour was an important factor in Barry’s decision, alongside the financial terms reportedly offered to him, including wages of around £100,000 per week. He later established himself as the Premier League’s record appearance holder.
David Silva Became a Major Missed Opportunity for Liverpool
David Silva’s arrival at Manchester City in 2010 became one of the club’s most influential acquisitions, but Liverpool had been pursuing the Spanish playmaker before City secured his signature.
Benitez had previously managed Valencia, a club known for developing gifted Spanish players. Silva was among the talents who attracted his attention, and the midfielder’s representatives confirmed in 2009 that discussions with Liverpool had been taking place over a possible transfer.
A move to Anfield appeared possible as negotiations continued. City, however, moved decisively the following year, agreeing a fee of approximately £24 million with Valencia, alongside substantial bonus arrangements, and offering Silva a lucrative contract.
City had not yet qualified for the Champions League, but their growing sporting ambitions and financial strength helped persuade the midfielder. Liverpool, meanwhile, were dealing with considerable instability under owners Tom Hicks and George Gillett.
Silva went on to enjoy a remarkable decade at the Etihad, winning 13 trophies and becoming one of the club’s most celebrated players. His contribution was recognised when City unveiled a statue in his honour in August 2021.
James Milner Joined City Before Becoming a Liverpool Favourite
James Milner was another major addition during City’s busy summer transfer window in 2010. The club also recruited players such as Yaya Toure, Aleksandar Kolarov and Mario Balotelli as they sought to build a squad capable of challenging for the biggest honours.
Milner followed former Aston Villa teammate Barry to Manchester, with City paying approximately £26 million for his services.
Liverpool were among the clubs linked with the midfielder, alongside Manchester United and Chelsea. However, City’s offer proved attractive, with a substantial transfer fee, Stephen Ireland moving to Villa as part of the deal and the prospect of doubling Milner’s wages all contributing to the outcome.
Milner was also drawn to the possibility of helping establish a successful new era at the Etihad. He went on to win two Premier League titles with City before leaving in 2015 to join Liverpool on a free transfer.
At Anfield, Milner became an important member of Jurgen Klopp’s squad, making him a distinctive figure in the transfer history between the two rivals.
Raheem Sterling’s Record-Breaking Transfer Sparked Controversy
Raheem Sterling’s move from Liverpool to Manchester City in 2015 was one of the most contentious transfers between the clubs during the Abu Dhabi ownership era.
The England forward had emerged as a major talent at Liverpool, particularly during the 2013-14 season, when his performances helped the Reds challenge for the Premier League title before City finished above them.
Speculation over Sterling’s future intensified, eventually developing into a bitter contract dispute. The forward attracted criticism over his handling of the situation, including an unauthorised interview with the BBC during the negotiations.
His agent, Aidy Ward, also drew heavy criticism from Liverpool supporters after an interview with the Evening Standard in which he dismissed concerns about the club’s public image and insisted Sterling would not sign a new contract, regardless of the proposed salary.
The dispute became increasingly acrimonious before City agreed a reported British-record £49 million transfer fee for the forward.
Sterling subsequently played a major role in City’s success, winning 11 trophies during his time at the club before departing for Chelsea in 2022.
Although Liverpool did not simply miss out on Sterling in the traditional transfer sense, his departure represented a significant moment in the rivalry, highlighting City’s ability to recruit a leading player directly from one of their closest competitors.
Transfer History Adds Another Layer to the Anfield Rivalry
Barry, Silva, Milner and Sterling represent four different examples of how Manchester City’s rise intersected with Liverpool’s ambitions in the transfer market.
In Barry’s case, Liverpool failed to secure a midfielder they had pursued before City intervened. Silva became a long-term target who ultimately chose the Etihad, while Milner first helped City establish themselves before later becoming a key Liverpool player. Sterling’s transfer, meanwhile, brought the rivalry into particularly sharp focus.
As the clubs prepare to meet again, those historical connections provide another dimension to an already significant fixture.
The financial verdict has intensified scrutiny of City’s achievements during the period under investigation, while the club’s appeal means the case remains unresolved. Against that backdrop, Sunday’s meeting offers a fresh chapter in a rivalry shaped by title battles, major signings and years of competition at the highest level of English football.
