From James Maddison & Wesley Fofana to Kasper Schmeichel and Jamie Vardy, the King Power side have recruited some truly exceptional talents over the years.
In the past decade and beyond, fans have witnessed brilliant arrivals that elevated the East Midlands club to the summit of English football, through frustrating battles to crack the Champions League, and down into the painful depths of relegation.
However, there have also been occasions where potential targets slipped away — either the player backed out, pushed for a different move, the selling club refused to negotiate, or Leicester simply couldn’t meet the financial expectations. Those are the stories we’re revisiting today.
While an exhaustive rundown would be unnecessary, here’s a concise list of the top five players Leicester City attempted to bring in but ultimately couldn’t secure. This is limited to the modern era — no ancient history here.
Leicester City’s unsuccessful pursuits:
1 | Ousmane Dembele
The gifted French winger Ousmane Dembele was once a major target for Claudio Ranieri following the Foxes’ historic Premier League triumph.
At the time, the teenager was starring for Rennes, and Leicester were eager to strengthen a title-winning squad they knew would be raided in the coming windows.
Dembele would’ve been a remarkable coup for the club. While he likely wouldn’t have stayed long-term, the potential resale value alone could’ve been transformative.
After Leicester’s failed attempt — which included a personal call from Ranieri — Dembele opted for Borussia Dortmund before sealing a £100m+ move to Barcelona.
The Ballon d’Or nominee currently averages 1.06 xG per 90 minutes and could have been pivotal in Leicester’s Champions League run had the transfer materialised.
Instead, after speaking directly with Ranieri, Dembele turned down the move himself, deciding the Bundesliga was the better environment for his growth.
2 | Harry Kane
England’s record-breaking striker Harry Kane was once within touching distance of becoming a Leicester player.
This one represents a massive financial what-if: imagine the profits from his inevitable future transfer.
Reports suggest Tim Sherwood blocked the move, even though Daniel Levy had agreed to sell Kane to Leicester for just £600,000.
This followed Kane’s loan spell during the 2012-13 campaign, where he managed two goals while competing with a strong strikeforce. Leicester’s bid was ready — and nearly accepted.
Since then, Kane has become Tottenham’s all-time top scorer, England captain, and arguably the most complete striker of his generation.
Had he developed at the King Power, the Foxes’ Premier League and European stories might have unfolded very differently — both on the pitch and financially.
3 | Arkadiusz Milik
Another missed striker opportunity. Leicester made two separate attempts to sign Milik — first in 2012, during their Championship days, and later after their Premier League title triumph.
The Polish forward rejected both approaches, later joining Ajax, where he scored 47 goals and registered 21 assists across all competitions before moving to Napoli.
He currently plays for Juventus and remains a respected finisher.
Had the Foxes landed him after their title win, Milik could’ve provided crucial support for Vardy and bolstered their Champions League push. The resale value — likely around £35m — would have been a bonus.
4 | Michael Keane
Another familiar name from Leicester’s loan days, Michael Keane impressed during his Championship spell in 2012-13 before moving to Burnley, where he became a defensive cornerstone.
After the title-winning season, Ranieri sought stability and targeted Keane. Leicester offered around £15m, but Burnley refused to sell. A year later, Everton snapped him up for £25m.
Keane evolved into an England international, averaging 2.5–3.5 successful defensive actions per 90 and maintaining composure under pressure.
He would’ve been an ideal long-term replacement in Leicester’s ageing defence — strong, calm, and consistent.
5 | Wilfried Zaha
Perhaps the most debatable name on the list, Wilfried Zaha was long linked to Leicester during his later Crystal Palace years.
A technically gifted, explosive winger, Zaha could’ve added flair and creativity to Leicester’s attack. The club were keen to bring him in permanently and even explored a loan move during his Galatasaray stint.
Now shining in the MLS, Zaha remains a player of immense talent — but his recent transfer path suggests Leicester may have dodged a risky investment.
Although Leicester City’s last decade has been remarkable, their failure to land some of these elite players cost them stability, goals, and potential windfalls that could have shaped their post-title campaigns.
There are, of course, many more missed opportunities — but these five stand out as the ones that could have truly rewritten the Foxes’ modern history.
Which names would you add to the list? Let Foxes of Leicester know your top picks and whether you’d have taken another chance on them, knowing how their careers eventually unfolded.