Conquering the UEFA Champions League (UCL) title is by no means an easy task, but doing it more than once in a row is even more of a challenge, one that only eight teams in history have managed: Real Madrid, Benfica, Inter Milan, Ajax, Bayern Munich, Liverpool, Nottingham Forest and AC Milan. Now, Chelsea will look to join the elite club after Kai Havertz’s 42nd minute strike against Manchester City back in May 2021 handed the ‘Blues’ their second-ever UCL. The job will be anything but easy, as the London-based institution will remember, since the last time they won the prestigious European competition, they weren’t even close to repeating.

After Chelsea defeated Bayern in the 2012 final via penalty kicks, the club quickly entered into a state of disarray during the 2012/13 season, even with the arrivals of Eden Hazard, César Azpilicueta and Oscar. Champions League-winning manager Roberto Di Matteo was sacked in November of that same year after losing 3-0 to Juventus in the group stage. Then, and now under the direction of Rafael Benítez, Chelsea finished third in their sector, below 'Juve' and Shakthar Donetsk, which made them the first reigning champions in the history of the tournament to not make to the knockout rounds. 

Benítez led the team to a UEFA Europa League win over Benfica in the final that season, and the UCL trophy then changed hands over to Bayern, who defeated Borussia Dortmund 2-1 with a late Arjen Robben goal in the 2013 final. Next season, Pep Guardiola took over from Jupp Heynckes as manager and signed Thiago and Mario Götze, among other players. The club won the Bundesliga and the DFB-Pokal double, but couldn’t replicate UCL glory and fell short in the semi-finals against eventual champions Real Madrid in a famous 5-0 aggregate thrashing. 

Real Madrid dominance

The ‘Merengues’ went on to beat local rivals Atlético de Madrid 4-1 in the final, with a last minute Sergio Ramos equalizer in regular time included, to win their tenth-ever Champions League. But, signing the likes of Toni Kroos, Keylor Navas and James Rodríguez wasn’t enough to win for the second time in a row in Europe’s grandest stage. The 2014/15 season saw the Spanish giants finish second in LaLiga, reach the Round of 16 in the Copa del Rey and lose in the UCL semi-finals against a Juventus side that included quality players such as Andrea Pirlo, Paul Pogba and Carlos Tévez. The ‘Bianconeri’ themselves then lost the final against Barcelona 3-1, a squad that boasted the powerful attacking trio of Lionel Messi, Luis Suárez and Neymar Jr. 

After winning the treble, along with their fifth-ever Champions League, the ‘Blaugranas’ brought in Ibrahim Afellay, Arda Turan, Alex Song and Aleix Vidal to strengthen the overall squad. The signings partly worked, helping Luis Enrique’s side to win the 2015/16 LaLiga and Copa del Rey titles. In Europe, Barcelona only made it to the quarter-finals of the UCL after losing 4-1 in aggregate against Atlético de Madrid, with an Antoine Griezmann double in the second leg sealing the fate of then-current champions. The ‘Colchoneros’ then reached yet another final, and once again fell short against Real Madrid. The penalty shootout win after a hard-fought 120 minutes signified the eleventh UCL title for the ‘Merengues’, who then began a remarkable era of European dominance, spearheaded by Cristiano Ronaldo. 

For the 2016/17 season, Madrid brought Álvaro Morata back from Juventus and gave Marco Asensio a more regular first team role after his loan to Espanyol. Zinedine Zidane’s magic worked to perfection once again, winning LaLiga and pummeling the ‘Bianconeri’ 4-1 in the 2017 UCL final, signaling the first time a team took home the coveted title consecutively since Arrigo Sachi’s historic AC Milan side won back-to-back Champions Leagues in 1989 and 1990. For 2017/18, Madrid lost Pepe, James Rodríguez, Morata and Danilo, but brought in Theo Hernández from Atlético de Madrid. In spite of finishing third in the league table and not winning the Copa del Rey, Zidane’s side once again triumphed in Europe by defeating Liverpool 3-1 in the UCL final, a match marred by the infamous Loris Karius mistakes and graced by the wonderful Gareth Bale bicycle kick goal. This was Ronaldo’s last-ever game for Madrid. 

The astonishing haul of four Champions Leagues in five years took a toll on Zidane, who left the club for the 2018/19 season. Julen Lopetegui controversially filled his spot, having been fired from the Spanish national team days before the 2018 FIFA World Cup for agreeing to sign for the ‘Merengues’ while he was still managing ‘La Roja’, according to Spanish Football Federation president Luis Rubiales. Lopetegui’s tumultuous reign only lasted until October, when Santiago Solari replaced him until the end of the year. The 13-time UCL winners finished third in LaLiga, reached the semi-finals of the Copa del Rey and were surprisingly booted out of the Champions League 5-3 in aggregate in the Round of 16 by a dynamic Ajax side. That year’s top winner in Europe was Liverpool, who edged out Tottenham in the 2019 final, 1-0. 

Chelsea's upcoming panorama

The 2019/20 season for the ‘Reds’ was focused mostly on domestic success, as Jurgen Klopp’s side won their first-ever Premier League title by beating Manchester City in the final standings. In the Champions League, Liverpool couldn’t defend their title after crashing out in the Round of 16 to Atlético de Madrid. The second leg of the tie was marked by an Adrían howler in goal and a Marcos Llorente brace in extra time. That year, Bayern won the UCL by defeating Paris Saint-Germain 1-0 in the final, thus capping off a tremendous year that also included Bundesliga and DFB-Pokal titles. As we now know, Chelsea was the team that won the 2020/21 Champions League, signifying yet another failure to win the most coveted club trophy two times in a row. 

The European Cup / Champions League has been played in full a total of 66 times, and won by 22 different clubs. Only eight teams have managed to win it twice or more times in a row, and only one (Real Madrid) has done so in the past 20 years. Chelsea are strongly putting themselves in the running of becoming number nine by bringing in Romelu Lukaku for $135 million, bolstering what was already a well-rounded squad. The ‘Blues’ started off the 2021/22 campaign by beating Zenit 1-0 with a lone Lukaku goal, but face stiff competition to win their third-ever Champions League, an arduous but achievable mission. In order to do so, they will first have to make it out of a group that also includes Juventus and Malmö. 

Then, the knockout stages, where they will face thougher oppostion. Their direct rivals in the competition have massively improved their squads, as well. Man City brought on Jack Grealish, PSG signed Lionel Messi, Georginio Wijnaldum and Sergio Ramos, and Liverpool once again have a fully fit squad. An entire UCL campaign can be decided on mere details, and Chelsea will need to improve on last year's performance if they wish to establish their own era of European dominance.