In 2012/13, Chelsea, managed by Rafael Benítez (interim after Roberto Di Matteo’s sacking), had a turbulent season following their UEFA Champions League triumph. The squad included stars like Frank Lampard, Juan Mata, Petr Čech, Eden Hazard, and Didier Drogba, blending experience with emerging talent. Chelsea finished 3rd in the Premier League, behind Manchester United and Manchester City, securing Champions League qualification. Domestically, they reached the FA Cup final but lost 1–0 to Wigan Athletic in a shock result. Despite struggles in the league and managerial instability, the season highlighted the squad’s resilience and set the stage for José Mourinho’s return in 2013/14.

In 2008/09, Chelsea, managed by Luiz Felipe Scolari (until February) and then Guus Hiddink as interim manager, experienced a turbulent yet ultimately stabilising season. The squad featured stars like Frank Lampard, Didier Drogba, John Terry, Petr Čech, and Michael Ballack, blending defensive strength with attacking firepower. Chelsea finished 3rd in the Premier League, behind Manchester United and Liverpool, while competing strongly in Europe. In the Champions League, they reached the semi-finals but were eliminated by Barcelona. Domestically, Chelsea won the FA Cup, defeating Everton 2–1 in the final. The season highlighted squad depth, resilience under managerial changes, and the emergence of Hiddink’s stabilising influence.

Between 2003 and 2005, Chelsea, under Claudio Ranieri, transitioned into a title-contending side following Roman Abramovich’s takeover in 2003. The squad featured Frank Lampard, Claude Makélélé, Jimmy Floyd Hasselbaink, Gianfranco Zola, and goalkeeper Carlo Cudicini, blending experience with emerging talent. In 2003/04, Chelsea finished 2nd in the Premier League, behind Arsenal’s unbeaten “Invincibles,” while demonstrating strong defensive organisation and attacking threat. In 2004/05, José Mourinho replaced Ranieri, revolutionising the team with tactical discipline, defensive solidity, and counter-attacking efficiency. Chelsea won the Premier League, ending a 50-year league title drought, and laid the foundation for a dominant era in English football.

Between 1999 and 2001, Chelsea, managed by Gianluca Vialli, were establishing themselves as a competitive Premier League and European side. The squad featured stars like Gianfranco Zola, Frank Leboeuf, Roberto Di Matteo, Gus Poyet, and goalkeeper Ed de Goey, blending creativity with defensive organisation. In 1999/2000, Chelsea finished 5th in the Premier League and made strong runs in domestic cup competitions, including reaching the FA Cup semi-finals. The following season, 2000/01, they improved to 6th in the league, while also competing in Europe. This period solidified Chelsea’s top-six status and laid the groundwork for Roman Abramovich’s takeover in 2003 and the club’s future successes.

Between 1997 and 1999, Chelsea, managed by Gianluca Vialli, were developing into a competitive force in English football. The squad featured stars such as Gianfranco Zola, Frank Leboeuf, Roberto Di Matteo, Gustavo Poyet, and goalkeeper Ed de Goey, blending technical flair with defensive organisation. In 1997/98, Chelsea finished 3rd in the Premier League, demonstrating attacking creativity and tactical discipline. The following season, 1998/99, they improved further, finishing 3rd again and consolidating their position in the top tier. This period marked the foundation of Vialli’s era, emphasising cup success, technical skill, and the club’s growing ambitions before the Abramovich era.

In 1996/97, Chelsea, managed by Gianluca Vialli, continued their rise as a competitive Premier League side. The squad blended creativity, skill, and defensive stability, featuring stars such as Gianfranco Zola, Frank Leboeuf, Gustavo Poyet, Roberto Di Matteo, and goalkeeper Ed de Goey. Chelsea finished 6th in the league, narrowly missing out on European qualification, but displayed consistent attacking flair and tactical organisation. In domestic cups, they began establishing a strong presence, setting the stage for future success. This season was key in building a cohesive, technically gifted team, laying the groundwork for Chelsea’s trophy-winning campaigns in the late 1990s and early 2000s.