Chilwell has been at Leicester City since the age of 12, and made his professional debut for the Football Club in a League Cup tie at Hull City in October 2015.
Since then, he has represented the Foxes in four competitions, including the UEFA Champions League, and has gone on to make 11 appearance for England’s senior team.
The Academy graduate is now a regular in City’s starting XI, and of the 95 Premier League appearances he has made to date, he selected five that most stand out to him, in addition to a memorable European night on Filbert Way.
First Premier League win in Leicester blue
Chilwell celebrates with Islam Slimani en route to a maiden Premier League win for the Club.
Having made his Premier League bow against Everton on Boxing Day 2016, Chilwell retained his spot in the starting XI for the clash with West Ham United five days later.
Playing the full 90 minutes, the Academy star helped City to their first clean sheet in the Premier League since early October as Islam Slimani struck the winner with 20 minutes gone.
“We played against Everton and then I think the West Ham game was maybe a midweek game, or it was only a few days after because it was around Christmas or New Year time,” Chilwell recalled.
“Obviously, it was the first clean sheet in a few months for the Club. [It was] my first win with Leicester in the Premier League and it was just a good day for myself.
“We obviously got the win, which was important, kicking on to the second half of the season.
“It was a great moment. You dream of playing in the Premier League when you’re younger, so the first home win, not even win, for the Club you played at since you were young in the Premier League is a special day.”
Introduced at half-time against Atlético
The left-back was brought on at half-time by Craig Shakespeare, and played a significant role in Jamie Vardy's equaliser on the night.
Chilwell was involved in one of the most exciting evenings in the Football Club’s history when Atlético Madrid came to town for the second leg of their UEFA Champions League Quarter-Final tie.
With City trailing 1-0 after Saúl Ñíguez’s early header, City’s No.3 was brought on at half-time and went close himself before his deflected shot fell to Jamie Vardy, who made it 1-1.
While City bowed out of the competition, losing 2-1 on aggregate, it was a proud night for many donning Leicester colours, including Chilwell.
“I remember warming up in the first half, and then at half-time, Craig Shakespeare, who was the manager at the time, told me that I’d be coming on for the second half and to go get warm,” he said.
“I was just excited, nervous, a lot of different emotions. The Champions League is a massive tournament that you look forward to hopefully playing in one day. Obviously, against Atlético, who are one of the biggest teams in Europe in the quarter-finals, it was a massive occasion for myself.
“It was a good time for me to try and have a good half on such a big stage in front of so many people. We lost the game (across two legs), but as a team, we played really well that night and could have won the game and progressed through.
“That was a great run from the Club to get to the quarter-finals. For myself, it was obviously another good day for me.”
A Boxing Day belter
Goals: Leicester City 2 Manchester City 1
All three goals from the Foxes' 2-1 victory over Manchester City in the Premier League.
Next on Chilwell’s list is another festive success, this time against eventual 2018/19 champions Manchester City on Boxing Day 2019.
Chilwell remembers the night mainly for the Blue Army’s celebrations that were triggered by the brilliant victory against Pep Guardiola’s star-studded side.
“It was a massive win,” Chilwell said. “Ricky (Ricardo Pereira) got the winner, which was obviously a great strike. It was an important win for us for momentum going into the second half of the season. It gave us a massive boost beating a team that obviously went on to win the league.
“[It gave us] massive belief, not just for the players, but obviously it was nice to do it at King Power Stadium in front of the fans as well. It was just a great day for everyone.
“Obviously [we were] very happy for Ricky to get the winner. It was just a great team performance and an all-round good day to see King Power Stadium rocking.”
Putting five past Newcastle
Goals: Leicester City 5 Newcastle United 0
Watch all the goals from the Foxes' 5-0 victory over the Magpies at King Power Stadium.
Moving onto the 2019/20 season, the first of two record-breaking wins for City came against Newcastle United on Filbert Way, with Chilwell again involved from start to finish.
City were in fine form having beaten Tottenham Hotspur 2-1 in their latest league outing thanks to James Maddison’s neat finish, and ran riot against the Magpies in late September.
Ricardo’s opener, a brace from Vardy, Paul Dummett’s own goal and late Wilfred Ndidi strike sealed a 5-0 success against Newcastle – City’s biggest-ever Premier League win at that point in time.
Chilwell said: “We started the season well, we were confident. The manager wants us to score a lot of goals, wants us to be exciting when we play as a team, so to get that 5-0 win at home, again, was a great day for the Club.
“It was the biggest win for the Club in the Premier League, and it was a great day for the fans. It gave us a good confidence boost that we were a good team that could score a lot of goals.”
Another record tumbles
Ben Chilwell vs. Southampton
Foxes defender Ben Chilwell opened the scoring in Leicester City's 9-0 Premier League win over Southampton.
However, City smashed their own record, and many others, under a month later when they travelled to the south coast to take on Southampton at St. Mary’s Stadium.
It proved to be a historic evening, with Chilwell opening the scoring on 10 minutes before setting up a further two goals in a 9-0 thrashing of the 10-man Saints.
“It was just a crazy night really,” Chilwell recalled. “Everything we did went our way. Every shot ended up being a goal, practically. Obviously, to get two assists and a goal myself was a great night and I think it was just such a good team performance by everyone.
“I remember at half-time, the gaffer, I’m not sure if we were four or 5-0 up, but I remember the gaffer saying at half-time not to let up, not to ease up, and to be clinical and try and get some more goals.
“I think maybe in the 70th or 80th minute, I remember Jonny Evans saying that we could get the record if we keep going. Obviously, it shows that we’re a clinical team now this season and obviously with a manager that wants us to be so ruthless. He’s given us that little edge this season that we maybe didn’t have before.
“There were some great strikes, and after the game, I just remember everyone saying it was just one of those nights that was always going to go our way.
“Everyone played well and there was a lot of goals. It’s just one of those nights that you remember as such a good team performance – kind of a perfect performance, really, from everyone.”
On target against Chelsea
Ben Chilwell vs. Chelsea
Ben Chilwell scored the Foxes' second goal in their 2-2 draw with Chelsea in the Premier League.
Finally, another fixture Chilwell found the back of the net in came on home soil this time as City hosted Chelsea in early February.
Two Academy stars were on target that day, with Harvey Barnes cancelling out the first of two Antonio Rüdiger headers before Chilwell fired Leicester in front on 64 minutes.
Chilwell felt the Foxes were good value for all three points, but he was nevertheless pleased to score his second Premier League goal of the season from left-back.
He added: “We were under the cosh for the first 15 to 20 minutes and then we grew into the game and probably should’ve won the game in the end, but like you said, it was a very end-to-end game and we had chances, they had chances.
“It was a very back and forth game and it was nice for me to get a goal as well. Yes, like you said it was a great game for the neutral, just disappointing that we couldn’t get the win.
“I saw the ‘keeper on the other side of the goal so I thought if I can get a good connection and hit the target then it’ll give myself the best chance to score.”
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