Dele Alli cuts a sporty figure as he steps out for some luxury shopping in Milan with mystery Cindy Kimberly lookalike – just weeks after they split
On Thursday, Dele Alli was seen spending a day in Milan with an unidentified lady, not long after parting ways with his girlfriend of three years, Cindy Kimberly.
Previously with Tottenham Hotspur as a midfielder (now playing for Como in Italy), the 29-year-old and his former partner, a 26-year-old model, have recently announced that they’ve ended their relationship, as confirmed earlier this month.
Following the observation that numerous photos with him were missing from her Instagram account, Cindy admitted that she and Dele had parted ways. She explained to GSM, “We’ve actually been apart for a short time now.
A few weeks following the announcement of their breakup, it was observed that Dele was casually walking through downtown Milan with an unidentified individual on a Thursday.
Dressed in a striking light blue Nike tracksuit, Dele spent a lavish afternoon shopping with a woman who resembled his former girlfriend, Cindy, very closely.
Accompanied by a small group of friends, she visited upscale boutiques Goyard and Loro Piana. For the occasion, she wore a pair of beige shorts and a white top, while shielding her eyes behind dark sunglasses.


Meanwhile, Dele was in Milan, Cindy took a flight to Saint-Tropez for a vacation with friend Chantel Jeffries following her split from the soccer player.
In the year 2022, it was made official that Dele and Cindy were a couple, with him continuing his soccer career at Everton in England at that time.
Following his transfer to Serie A team Como in January as an attempt to rejuvenate his career, Cindy relocated to the northern part of Italy together with Dele.
Since their move, it’s been evident that they have taken a liking to each other. The Sports Illustrated cover model frequently shares photos of herself and Dele on various occasions.
In 2023, the footballer candidly shared about his tumultuous childhood, during which he suffered sexual abuse starting at just six years old. Throughout all this, Cindy had provided unwavering support.
Additionally, she continued to support him during a very open conversation with Gary Neville where he discussed his dependency on sleeping pills and personal mental health struggles, both of which were presented candidly.
Speculation about a possible separation surfaced earlier this month, following Cindy’s removal of several photos depicting the couple, among which was one taken in April showing them basking in the sun at Como.
After a brief period, she verified their separation, informing GSM that they had been estranged for quite a while.




Although Dele had hoped that his transfer to Como would rejuvenate his career in preparation for the following year’s World Cup, events since his relocation to Italy have not unfolded as he may have anticipated.
In their single outing for the team this season against AC Milan, the former Spurs midfielder received a red card for a careless tackle on Ruben Loftus-Cheek, an English player.
In his first game for Como after a hiatus of over two years, Dele was on the field for merely 10 minutes. Post-game, manager Cesc Fabregas criticized Dele for a significant error.
Fabregas mentioned that Dele Alli possesses the ability to net goals, but he may not have fully earned this chance since he’s only been training with us for a fortnight and still has room for improvement.
‘It is a grave mistake, one that we should not see from a player of his experience.
During a pivotal stage of our fight for 2-2, he received an unarguable red card, which left our team short-handed with only ten players.
‘That is the most negative thing about this evening, but we keep going.’

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2025-06-21 11:48