The 27-year-old is another to have fallen victim to the Blues’ chaotic recruitment drive this summer. He and a range of others, including the publicly ousted Raheem Sterling, have essentially been told to seek pastures new.
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Chilwell joined Chelsea in 2020 for a hefty £50million from Leicester City. But the injury-plagued England ace has failed to stake a claim to the first-choice left-back spot, being replaced by Marc Cucurella, who enjoyed a stellar Euro 2024 with Spain.
Erik ten Hag’s United have emerged as a potential landing spot. And if his past comments – that it was the Red Devils who helped him fall in love with football – are anything to go by, then it’s a transfer he would welcome.
“I used to go to Man United games, funnily enough, with my dad, who supported them,” Chillwell told Chelsea’s official website back in June 2023.
“The first one, I can’t remember who it was against, but it was a Man United game. We always used to go to the Champions League ones after school, so it would have been a Champions League game at Old Trafford. That’s the first one I remember. Having your first one in the Champions League is pretty good.
“We used to go by train, we would have to take about four different trains straight from school, and just about make it for kick-off, then get about four different trains on the way home as well, get home for one o’clock in the morning, straight into school the next morning again, but they were brilliant memories.”

Chilwell joined Leicester at 12, working his way up to make his first-team debut under Claudio Ranieri in 2015. During the club’s miraculous league title success, he spent time at Huddersfield Town on loan and with the Foxes’ academy side.
He did feature in a two-legged loss to Tottenham in the FA Cup that year, which earned him endless plaudits for a composed performance. On the back of this showing, he penned a new five-year deal and was handed a league debut later in 2016.
He made 100 appearances in the Midlands before Chelsea snapped him up in 2020, where he has since won the Champions League. It wasn’t the Foxes, however, that first ignited Chilwell’s love for the game – that accolade goes to the Red Devils.
“It’s nights like that [ watching United] which make you fall in love with football,” Chilwell continued. “Going straight from school, six- or seven-hour round trip, just to go and watch a game. Just being starstruck and in awe of all the players, that’s the kind of night which makes you love football, I guess.
“I was focused all on the pitch, trying to find my favourite players at the time and just seeing them in person was crazy. Just the feeling of awe at the position they were in and looking up to them like gods. Of course, the atmosphere’s amazing, but I was definitely one of those people focused on the pitch and the players.”
Ten Hag’s team only hold reported interest in Chilwell currently. But, with the player on Chelsea’s transfer list and United’s first-choice left-back Luke Shaw currently sidelined again along with Tyrell Malacia, it could be a move to keep an eye on.