Every transfer window brings speculation, hope, and sometimes heartbreak for fans dreaming of a marquee signing. But football history is littered with deals that seemed destined to happen, only to collapse at the final hurdle — sometimes for the better, sometimes leaving supporters wondering what might have been.
One of the more recent examples involves Nigerian striker Gift Orban, who in 2023 was among the most sought-after young forwards in Europe. Then 21 and playing for Belgian club Gent, Orban had already built a fearsome reputation, having scored 16 goals in 22 games for Norwegian side Stabaek before notching 20 in 22 for Gent. His purple patch included a four-goal haul against Zulte Waregem and a lightning-fast hat-trick against Istanbul Basaksehir in the Conference League, completed in just over three minutes — a Uefa club competition record at the time.
With Harry Kane departing for Bayern Munich, Tottenham were linked with Orban as a potential successor, even drawing comparisons in media coverage that questioned whether he could become a global star. However, newly appointed manager Ange Postecoglou and the club balked at Gent's £25m asking price, and the deal never materialized. Since then, Orban's career has taken a winding path through Lyon, Hoffenheim, and a loan at Verona, before a fresh loan move to newly promoted Turkish side Amedspor. His output has been modest compared to his breakout form, though a productive loan spell in Serie A hinted his talent remains intact.
Orban's case is just the latest in a long line of near-miss transfers that shaped — or failed to shape — football history. In 2009, Manchester City's newfound financial muscle nearly landed them Brazilian playmaker Kaka in a deal reportedly worth £108m, which would have shattered the existing transfer record. The move fell through, and Kaka instead joined Real Madrid for £56m later that year, going on to win La Liga and the Copa del Rey before later spells at AC Milan and Orlando City.
Bolton Wanderers, then enjoying a golden era under Sam Allardyce, came close to signing Brazilian World Cup winner Rivaldo in 2004. The player himself spoke enthusiastically about the move, saying, "I want the challenge of trying to get Bolton into Europe for the first time in their history. It is an exciting time." Ultimately, he chose Olympiakos instead, while Bolton finished sixth in the Premier League that season and reached the last 32 of the Uefa Cup regardless.
Perhaps the most famous case of transfer regret belongs to Blackburn Rovers, who in 1995 turned down the chance to sign a young Zinedine Zidane from Bordeaux. Owner Jack Walker reportedly dismissed the idea, asking, "Why do we need Zidane when we have Tim Sherwood?" Zidane went on to become one of the greatest players in history, winning World Cups, European Championships, and Champions League titles.
Liverpool supporters, meanwhile, might reflect on two near-departures and one near-arrival. Steven Gerrard flirted with a move to Chelsea in 2005 before staying at Anfield for personal reasons, later making over 700 appearances for the club. Years later, Jose Mourinho admitted missing out on Gerrard was one of his biggest transfer regrets. Liverpool also came close to signing Kylian Mbappe in 2017, with the France striker admitting his mother supported the club. Despite Liverpool's efforts, including arranging private travel for his family, Mbappe chose Paris Saint-Germain, where he won six consecutive league titles.
Fulham's brush with Antoine Griezmann in 2014 is another footnote in transfer folklore. A £12m enquiry for the Real Sociedad forward went nowhere, and Fulham instead spent the same fee on Kostas Mitroglou, who managed no goals in three Premier League appearances before the club's relegation. Griezmann, by contrast, thrived in Spain, later helping France win the 2018 World Cup.
Based on reporting from BBC Sport.