On the day Chelsea and Zenit St Petersburg meet for the very first time, we look back at the small number of players, and the one manager, who have represented the Blues of London and the Blue-and-Whites of Russia’s cultural capital.

There are over 1500 miles between Stamford Bridge and the Krestovsky Stadium, and the difference in cultures and leagues is perhaps reflected by the lack of crossover between the two clubs. Still, there has been some in the past decade or so, and here we focus on those individuals, starting with two players who are good friends and won the English and Russian Premier Leagues together…

Yury Zhirkov and Branislav Ivanovic

Yury Zhirkov was the second Russian to sign for Chelsea in our history, after Alexey Smertin, when he arrived from CSKA Moscow in the summer of 2009.

The left-sided player had starred at the European Championships 12 months earlier as an exciting Russian side reached the semi-finals. He had also played a crucial part in CSKA’s successful UEFA Cup campaign of 2004/05, even scoring in the final against Sporting Lisbon.

Possessing good crossing ability and a willingness to dribble with the ball at speed, Zhirkov was signed by Carlo Ancelotti to offer competition to Ashley Cole at left-back, and Florent Malouda ahead of him.

Unfortunately, injuries consistently disrupted Zhirkov’s time at the Bridge, and we only fleetingly saw the best of him. Probably his best run of form came as winter turned to spring in 2010.

With Cole out injured, Zhirkov was able to feature consistently in the February, March and April of that year, and put in outstanding performances in crucial back-to-back victories over Aston Villa (7-1) and Manchester United (2-1) that put us top of the league with a handful of games remaining. He was an unused sub in the FA Cup final that secured us the Double, having played the full 90 of the semi-final success over Villa.

Ironically Zhirkov scored his solitary Chelsea goal in Russia, against Spartak Moscow, in the following season’s Champions League group stage. It was a spectacular effort, too, and showed just what he could offer the team when fit.

He returned to Russia in 2011 to join Anzhi Makhachkala, before spending three years at Dynamo Moscow. In 2016, he moved to Zenit where he spent five years before leaving the club this summer having added seven more winners’ medals to his collection.

For two-and-a-half of his five years in St Petersburg, Zhirkov called Branislav Ivanovic a team-mate again after the two seasons they spent together in SW6, during which time they became firm friends. Ivanovic regularly helped translate for the man who had left his homeland for the first time.

Like Zhirkov, Ivanovic joined the Blues from a Moscow club – Lokomotiv – but unlike Zhirkov, Ivanovic truly reached his potential at Chelsea, becoming a club legend during his nine years in London. He won it all, including the Premier League twice, and famously headed the winning goal in our 2013 Europa League triumph.

He signed for Zenit in 2017 and was quickly installed as captain, leading the club to league success in both 2018/19 and 2019/20, before returning to England to join West Brom.

Both Zhirkov and Ivanovic are currently free agents, with no indication, at 38 and 37, they are about to retire.

Andre Villas-Boas

Andre Villas-Boas arrived at Chelsea shortly before Zhirkov departed for Anzhi, replacing Ancelotti in the dugout at the age of 33.

Despite some signs of promise, his efforts to change our playing style, and in the process often opting for youth over experience, didn’t pay off. He was relieved of his duties in March 2012 with the Blues outside the top four and in a perilous position in the Champions League having been well beaten in Naples.

Two years later he took over the reigns at Zenit, leading them to the title in his first full season in Russia.

His second and final campaign saw Zenit reach the last 16 of the Champions League and win the Russian Cup, emphatically beating CSKA in the final. He has since managed Shanghai and Marseille.

Mateja Kezman

Mateja Kezman spent a season at Stamford Bridge in 2004/05, and then just a few months in St Petersburg, where he scored twice in 10 appearances during a loan spell from PSG towards the end of 2009.

At Chelsea the striker finished with seven goals in 41 appearances, later declaring it the best period of his career despite not hitting the heights he had in Holland. He retired in 2012.