Yaya Toure to Arsenal
Back in 2003, as the best of 14 Ivorian players at Belgian side Beveren, Toure went on trial to Arsenal, and even played for the Gunners on trial against Barnet.
The midfield powerhouse delivered an unremarkable display, described by Arsene Wenger as ‘completely average’, and reportedly missed a fine chance to score the winner.
The French coach was understood to still be keen on the youngster—despite not clearly understanding how he’d use him—but ultimately work permit complications prevented a deal being done.
Yaya missed out on the chance to line up alongside brother Kolo—although they would eventually unite at Manchester City—but would blossom into the world’s finest central midfielders after leaving Beveren for Metalurh Donetsk later that year.
Lucas Radebe to Manchester United
"Everyone should be interested in Lucas," said Sir Alex Ferguson about the Leeds United defender, according to Radebe himself, and Manchester United even made a move to sign the centre-back during his peak years at Elland Road.
Ultimately, the South Africa international turned down the Red Devils out of loyalty to their bitter rivals across the Pennines, missing out on the chance to follow Eric Cantona’s path from Leeds to Old Trafford.
United were keen on recruiting the defender for £10 million, according to the Express, and Radebe ultimately ended his career without a major club honour.
Alex Song to Liverpool
At the end of his second season at Barcelona, Song was the subject of reported transfer interest from Liverpool, with the Reds understood to be keen to bring the ex-Arsenal man back to the Premier League on loan.
Ultimately, he moved to West Ham United, impressing with the Hammers as they finished 12th, and ending the campaign as the joint sixth most effective tackler in the division.
Liverpool ultimately recruited Emre Can, and while the Germany midfielder did impress at Anfield, the Reds ended the season in sixth—far short of their sec0nd-placed finish the season before.
Richard Kingson to Asante Kotoko
In the final days of his career, Ghana goalkeeper reiterated his desire to represent Asante Kotoko, having previously outlined his admiration for the club’s supporters.
At one point, a deal appeared close—according to local reports—and it could have been an emotional final stop-off on the keeper’s two-decade career.
Ultimately, the stopper hung up his boots without ever having represented the Porcupine Warriors.
Sulley Muntari to Manchester United
Muntari trialled at United at the very start of his career, having impressed for Ghana’s U-20 team at the 2001 World Youth Championship in Argentina.
Ultimately, he signed for Udinese, and would go on to win the Champions League and the Serie A title at Internazionale.
The Black Star could come back to haunt United in the quarter-final of the 2007-08 FA Cup, scoring a 78th-minute penalty winner at Old Trafford to dump the Red Devils out of the competition.
United were also reportedly keen on recruiting the tenacious operator later in his career, but the transfer talk came to nothing.
Didier Zokora to Arsenal
Zokora became an instant fan favourite after arriving at Tottenham Hotspur in the summer of 2006—having impressed at the World Cup—when he revealed that he’d turned down Arsenal before making the move to White Hart Lane.
Ostensibly arriving as a replacement for United-bound Michael Carrick, Zokora could have been an ideal Wenger signing—boasting technical quality, flair and flamboyance in abundance.
"I listened to an offer from Arsenal but decided Tottenham was the club I wanted to be at,” said the £8.2 million man. “One of the big things was that Tottenham really showed they wanted me and that really pleased me."
One wonders whether, after leaving Spurs with just a League Cup winner’s medal, the Maestro regretted his decision.
Wael Gomaa to Blackburn Rovers
Mark Hughes brought several major African talents to the Premier League, and is responsible for introducing the likes of Christopher Samba, Benni McCarthy, Stephane Mbia, Sambia Diakite and Rafik Halliche to England.
One player who he failed to get over the line is Egypt’s Gomaa, one of the most decorated African players ever to play the game.
The centre-back came to Blackburn Rovers on trial during the 2006-07 season, although Hughes ultimately opted against recruiting the stopper.
Egyptian players historically tended not to travel too well away from their homeland, but Gomaa’s defensive fundamentals and tenacity could have made him a Premier League success story.
Stephen Appiah to Tottenham Hotspur
Midway through the 2008-09 season, Ghana great Appiah came to trial with Harry Redknapp’s Spurs, with a view to securing a permanent deal.
The box-to-box operator—who was part of the Ghana team that reached the World Cup quarter-finals in 2010—could have been a magnificent addition for the Lilywhites, although they ultimately opted to recruit Honduras international Wilson Palacios.
The injury-prone Appiah later revealed that he had opted against extending his trial period at Spurs, despite a request from the Londoners for him to do so.
Taye Taiwo to Bayern Munich
Having been signed by Olympique de Marseille to replace Bayern-bound Bixente Lizarazu, the left-back was later targeted by the German giants themselves in 2010.
At the time, Taiwo was entering the final year of his deal at OM, and was hot property, having been named in the Ligue 1 Team of the Season in both 2008 and 2009.
He ultimately moved to AC Milan, and began a career downturn that has seen him subsequently turn out for Queens Park Rangers, Dynamo Kyiv and Bursaspor among others.
The 35-year-old is currently on the books of Finnish side RoPS.
Mustapha Zitouni to Real Madrid
In March 1958, then-Real Madrid president Santiago Bernabeu was so impressed with a performance by Franco-Algerian defender Zitouni—then representing France—against Spain that he reportedly offered 50 million francs to recruit the defender from Stade de Reims.
During the match, Zitouni had silenced the iconic Alfredo Di Stefano in a way that few had managed before, and denied the Spanish a certain winner.
Zitouni however, had other priorities, and instead opted to join with Algeria’s legendary FLN (National Liberation Front) team and went on to play such a critical role in carrying the North African nation to independence.