Football’s transfer market is a museum of oddities. Every summer we gather in front of the glass, pointing at curios that still make us blink. Some are bureaucratic accidents. Some are born of desperation. Some are the kind of left-field moves that sound like a mate winding you up in the pub. Here are nine that genuinely happened, each of them a reminder that the game’s pathways are rarely straight lines.
Crazy times bring crazy transfers
Rúben Amorim: Benfica to Al-Wakrah on loan
Before he was the bright young coach on every big club’s shortlist and then the man in the Manchester United dugout, Amorim’s playing career drifted into the desert. Benfica, knee injuries, and a messy disciplinary spell led to a season-long loan at Al-Wakrah in Qatar in 2015. He even captained them. A year later he was back home, and by 2017 he had retired as a player. The twist is what came next: a meteoric coaching rise that eventually brought him to Old Trafford in November 2024. He might also be the only United manager who turned up and somehow ended up with more hair than when he arrived, which is some achievement given that job usually takes it away.
Frank Lampard to Manchester City
Lampard leaving Chelsea was emotional enough. Lampard turning up in sky blue, scoring against Chelsea at the Etihad, and barely celebrating felt like a script doctor had gone rogue. The arrangement was complicated, routed via New York City FC and City Football Group technicalities, but the headline was simple: one of Chelsea’s greatest played a season for City and changed a title race mood with a late equaliser. It was announced as a short-term stay, then extended to the end of the Premier League season. City later clarified the paperwork wasn’t a standard MLS loan at first, which only added to the weirdness.
Mascherano and Tevez to West Ham on the same day
Deadline day 2006. West Ham, fresh from mid-table comfort, unveiled two of the hottest properties in South American football. It was astonishing, then it got messy. The third-party ownership arrangements around the deals dragged the club into a storm that rumbled for years. The Premier League fined West Ham a record £5.5 million, yet no points were docked. Tevez scored the goal at Old Trafford that kept the Hammers up and pushed Sheffield United down, a fact that fuelled litigation and a long tail of bitterness. It remains the most notorious case study in how opaque ownership structures can distort competitive balance.
Edwin van der Sar to Fulham
Some transfers are surprising at the time, others become more baffling with hindsight. Juventus selling Van der Sar to newly promoted Fulham in 2001 for around £7 million belongs in both categories. He had been displaced by Gianluigi Buffon in Turin, yet the class was obvious. Four seasons and 127 games later he left Craven Cottage for Manchester United for a fraction of that fee and promptly became the most reliable figure of the post-Schmeichel era. Imagine Sunderland today picking up someone of Donnarumma’s pedigree from PSG. Fulham did the 2001 version of that.
Martin Braithwaite to Barcelona
In February 2020, with Luis Suárez and Ousmane Dembélé both injured, Barcelona activated an emergency Spanish rule that allowed them to sign outside the window. They paid Martin Braithwaite’s €18 million release clause at Leganés, registered him for LaLiga only, and carried on. Leganés were not allowed to replace him under the same rule and were furious. The optics were stark: a super-club solving a crisis by weakening a relegation battle rival. The rule was scrapped soon after. Braithwaite, for his part, worked hard and made the most of a surreal situation.
Ben Greenhalgh: Welling United to Inter Milan
You could watch football for a lifetime and not see another story like this. In 2010, a teenager from Welling United won a Sky reality show, earned a contract at Inter, trained under José Mourinho’s staff and travelled with the squad that won the treble. Greenhalgh never made a first-team appearance, but he came home with a Champions League winners’ medal after being part of the travelling party for the Bernabéu final. He later carved out a nomadic lower-league career and now manages while still playing. It is a tale told with a grin: a back-of-the-net dream that actually happened.
Serge Aurier: Galatasaray to Persepolis
Aurier has always taken the scenic route. After Tottenham, Villarreal and Nottingham Forest came a short Galatasaray stint, then in 2025 a move that raised eyebrows: Persepolis of Iran. The club rolled out the welcome, the Iranian press lit up, and within days there were conflicting reports around his availability that he publicly pushed back on while training. For a right-back who once patrolled the Parc des Princes, Tehran felt like a left-field final act and a reminder that careers rarely move in straight lines.
Serge Aurier (32) – Galatasaray to Persepolis (Iran) (2025) pic.twitter.com/REmDsf5WQZ
— Transfersthathappened (@actualtransfers) August 22, 2025
Eric Maxim Choupo-Moting: Stoke City to PSG
Stoke were down, Choupo-Moting’s contract was winding up, and on the window’s final day in 2018 Paris Saint-Germain snapped him up. On paper it looked odd. In practice he became a useful squad forward, a reliable personality, and the author of one of the Champions League’s most dramatic cameos. With PSG heading for another quarter-final exit in 2020, he arrived from the bench to score the 93rd-minute winner against Atalanta in Lisbon. From Stoke relegation to PSG hero. It made sense in the end. Football often does, just not immediately.
Ronaldinho to Querétaro
Even by his standards, this was a vibe. In September 2014, Ronaldinho signed a two-year deal with Querétaro, took up residence in a hotel, and turned Liga MX weekends into an event. The lasting image is from the Azteca in April 2015. He came off the bench for Querétaro, scored twice in a 4-0 win over América and received a standing ovation from one of the most unforgiving stadiums in the world. A brief, brilliant encore for a footballer who turned joy into a profession.
Happy Birthday to the magician who made football even more beautiful! 🎩
— 365Scores (@365Scores) March 21, 2025
Ronaldinho—the name that means joy, skill, and a smile that captivated the world! A legend like no other! 🔥✨ pic.twitter.com/Fox4kWYBPz
Why these transfers endure
They stick because they bend expectation. Lampard in sky blue, Van der Sar pausing at Fulham on the way to Old Trafford, Braithwaite as an emergency solution at the Camp Nou, two Argentine stars arriving at Upton Park together, a reality-show winner with a Champions League medal, Ronaldinho basking in Azteca applause, Aurier landing in Tehran, Choupo-Moting becoming PSG’s late-game saviour, and Amorim detouring through Al-Wakrah before coaching United. None of them are myths. They happened, paperwork and all. Which is why, every summer, we peer through the museum glass again, wondering what the next absurd little exhibit will be.
By Nicky Helfgott – NickyHelfgott1 on X (Twitter)
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