Ben Chilwell’s itinerary for the coming weeks includes a trip to Porto for the Champions League final against Manchester City followed by hopefully quite a few nights at Wembley playing for England at Euro 2020.
But none of those stellar occasions will make him quite as nervous as facing former club Leicester City in this Saturday’s FA Cup final.
‘The FA Cup against Leicester is the big one for me. To play against them in the final… there has not been a game in my career that I’ve wanted to win more,’ he told MOTDx this week.
Ben Chilwell has enjoyed an impressive first season in Chelsea colours and could end it by winning both the FA Cup and the Champions League this month
It was Frank Lampard who brought Chilwell in from Leicester last summer in a £50m deal
There were concerns over his place at first but Chilwell has won the trust of Thomas Tuchel
Not enough time has passed since Chilwell’s £50million move from Leicester to Chelsea last August for it to be any other way.
The left-back is still close to his former team-mates and he admitted that losing to them at the King Power Stadium back in January was the low point of his Chelsea career so far.
That 2-0 defeat proved to be Frank Lampard’s final Premier League match in the Chelsea job.
Chilwell had been Lampard’s undisputed first-choice at left-back – unsurprising given he signed him – but for a short time when Thomas Tuchel came in, that looked in doubt.
The German manager wanted to give everyone a clean slate and that offers Marcos Alonso, frozen out by Lampard, a route back into the team.
By Chilwell’s own admission, Alonso was far better suited to playing as a wing-back in a defensive five.
Tuchel restored Marcos Alonso to the Chelsea side at first, favouring five at the back
But Chilwell has regained his place on the left, featuring in all of Chelsea’s important games
‘I’ve not really played in a back five before. I played the first game when he [Tuchel] came in against Wolves, didn’t have my best game, wasn’t really sure on positioning, where I was meant to be,’ he told Soccer AM this week.
‘So when I came out the team I just took it as an opportunity to learn in training. Learn off Marcos, what he is doing in games. Ask the manager questions, what he thinks I can do to improve my play.
‘It just gave me that little extra push to give that little bit more to show him you should be playing.
‘And when you get your opportunity to play, make sure you take it.’
It soon became apparent to Tuchel that Chilwell could do the business as a wing-back and he has been preferred in every game of any note since.
Tuchel thanks Chilwell after he scored the second goal in Chelsea’s first leg win over Porto
He also completed both legs of the Champions League semi-final win over Real Madrid
May 15 Leicester City (Wembley)
FA Cup final
May 18 Leicester City (H)
May 23 Aston Villa (A)
May 29 Manchester City (Porto)
Champions League final
He played in both legs of the Champions League quarter-final against Porto and the semi-final with Real Madrid, against Manchester City in the FA Cup semi-final, and in big league games with Manchester United, Liverpool and Arsenal. First choice again, beyond all doubt.
So while there have been murmurings that Tuchel was so annoyed with his team’s performance in the 1-0 loss to Arsenal on Wednesday, chances are Chilwell will line up against his old club at Wembley.
Chilwell joined Leicester’s academy at the age of 12 and they gave him the perfect grounding in the game.
It was Claudio Ranieri that handed the teenager his first-team debut in a League Cup match during the 2015-16 title-winning season that propelled him and his team into immortality.
He was linked with a move to Liverpool in the summer of 2016 but instead penned a new five-year contract with Leicester.
Chilwell pictured with Leicester manager Brendan Rodgers following a match last season
Chilwell scored a stunning goal for Leicester away to Watford shortly after the restart last year
When Chilwell caught the eye on his Premier League debut against Everton in December 2016 he was a rare bright point in a season in which the reigning champions flirted with relegation.
Gradually, he displaced Christian Fuchs from the left-back position and would go from strength to strength in the three subsequent seasons.
His crossing developed during that time and the assists started to flow. His finishing, too, not least with the left-footed rocket he scored at Watford just after lockdown last season.
Such moments convinced Chelsea to make another swoop on Leicester and Chilwell duly followed N’Golo Kante and Danny Drinkwater in treading the path from the East Midlands to Stamford Bridge.
Chilwell (left) slides in to celebrate with Mason Mount and Christian Pulisic against Real
An awful lot has happened in the meantime but Chilwell has enjoyed a fine season and it could yet conclude with the first two medals of his career.
Not that Leicester are exactly struggling without him. They sit above Chelsea in the Premier League table following another positive campaign under Brendan Rodgers and will be doing their utmost to win the FA Cup for the first time.
The emergence of James Justin and then 19-year-old Luke Thomas in Chilwell’s old position has shown yet again Leicester’s ability to move on following big name departures.
But Chilwell has undoubtedly taken a step up and delivered the goods. He could be set for one hell of a summer.