Eyebrows were raised when Stockport’s assistant coach Andy Mangan appeared on the verge of a sensational move from the League One club to Real Madrid last week, only for the deal to be scuppered by work permit issues related to Brexit regulations. But where Mangan’s application failed, others have succeeded in taking the unlikely path from the Football League to some of the biggest clubs in Europe.

Dale Jennings (Tranmere to Bayern Munich, 2011)

After a string of good performances in League One at Tranmere, the former Liverpool youth player joined Bayern in 2011, becoming only the second Englishman after Owen Hargreaves to sign for the German club. The deal very nearly fell through after Jennings failed his medical in Bavaria. “They didn’t want to sign me,” Jennings said last year. “My agent, he did well, he asked them: ‘You’re the best medical staff in football, and you’re failing him over a hernia?’ They said: ‘We can look after him’ and they put it through.”

Beset by injuries, homesickness and the language barrier – “I tried to learn for about six months but I felt it was affecting my play and it got too much for me” – Jennings never played competitively for the first team and returned to England two years later with Barnsley, before stints at MK Dons, Runcorn Town and most recently Prescot Cables.

Tyrone Mears (Derby to Marseille, 2008)

Mears left Derby in controversial circumstances after it was revealed that the right-back had to climb through a window and crawl past Paul Jewell’s office at the second-tier club’s training ground to collect his boots before sneaking away to meet Marseille officials. Mears was later fined six weeks’ wages by Derby for attending a trial without consent but eventually a season’s loan to Marseille was agreed. Mears had to wait until January for his debut but scored the winning goal in extra time against Ajax in the Uefa Cup to send Marseille to the quarter-finals. However, a permanent deal didn’t materialise and Mears ended up at Burnley before further moves to Bolton and the MLS.

Brian Deane (Sheffield United to Benfica, 1998)

The first player to score a Premier League goal re-signed for Sheffield United for £1.5m in 1997 as the Blades pushed for promotion. After Deane scored 10 league goals in 24 second-tier games, Graeme Souness, the Benfica manager, came calling with a £1m bid. “Obviously there were some nerves because I knew how big the club was but I didn’t want to have regrets,” said Deane in 2022. “I was 29 at the time and for me it was about making stories. It was something I couldn’t turn down and I hoped I could get a move on to Spain or Italy, but that didn’t materialise.” Despite Souness’s squad having a distinctly British feel, with Dean Saunders, Gary Charles, Steve Harkness, Mark Pembridge, Michael Thomas and Scott Minto also in the side – and Deane’s record of seven goals in 14 league appearances in 1997-98 that included excellent strikes against Sporting and Porto – Deane lasted only nine months in Portugal, returning to England with Middlesbrough in October 1998.

Jude Bellingham (Birmingham to Borussia Dortmund, 2020)

Birmingham were mocked for retiring Bellingham’s No 22 shirt when he left his boyhood club for Dortmund in July 2020 after 44 appearances, but that doesn’t seem so silly now, with the Englishman at Real Madrid and regarded as one of the best players in the world. The German club made him football’s most expensive 17-year-old, paying an initial £22.5m for the midfielder, beating off fierce competition from Manchester United, who offered Bellingham a tour of their training ground with Sir Alex Ferguson. Bellingham chose Dortmund because they guaranteed immediate first-team opportunities. “There’s not a club in world football better at developing young talent for the next level,” he said upon visiting the Westfalenstadion for the first time. And develop he did. Bellingham scored on his Dortmund debut and was an England international by Christmas. We all know what happened next.

Fabio Borini (Sunderland to Milan, 2017)

This one just about sneaks into this list on account of Sunderland being relegated to the Championship in 2016-17, so although Borini is not really a Championship player, the Italian was hardly sought after having scored 16 league goals in five years in England with the Black Cats and Liverpool. So it was a huge surprise when two giants of Italian football, Lazio and Milan, showed interest. “We had started a negotiation with Lazio, Fabio had talked with both [the sporting director Igli] Tare and [manager Simone] Inzaghi,” said the former Sunderland director Roberto De Fanti. “But then Milan presented an unmissable offer and the deal ended in 24 hours.” Lazio were unwilling to meet Borini’s £35,000-a-week wage demands, but Milan agreed a £5.3m deal for an initial loan that was made permanent a year later. Borini’s goal record didn’t improve in Milan, with eight goals in 75 appearances, before a move to Verona in 2020.

And one of the weirdest ones the other way …

Allan Simonsen, Barcelona to Charlton, 1982

In 1982, Allan Simonsen was in his prime, aged 29, having just scored the goal to win Barcelona the European Cup Winners’ Cup. But the Dane, who won the 1977 European Footballer of the Year award (now the Ballon d’Or), beating players including Kevin Keegan and Johan Cruyff that year, was the odd man out after Barça bought a little Argentinian named Diego Maradona. With the Spanish club able to field only two foreign players in a starting lineup (the German superstar Bernd Schuster had the other spot), Simonsen was remarkably sold to second-tier Charlton, whose chairman, Mark Hulyer, gambled that the £300,000 fee might increase gate receipts. Simonsen reportedly rejected Real Madrid and Tottenham because he wanted a club with less scrutiny and attention. Despite some inspired performances for the Addicks which included nine goals in 16 appearances, Charlton’s financial gamble didn’t work and the club couldn’t afford his wages. Simonsen left shortly after to sign for his boyhood club, Vejle BK, in Denmark, and the Addicks faced bankruptcy in 1984 and were forced to move out of their stadium of 60 years, The Valley, in 1985.