Listen to episode 13 of the podcast, on the most unexpected and shocking transfers in living memory.

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Judging by the first transfer deadline day under the Premier League’s new rules, meaning clubs have to have their business sorted before the season begins, we can expect fewer last-minute, dramatic signings in the summer windows to come.

In our latest show we decided to look back on some of the more shocking and mental transfers down the years, the ones that few people could have ever envisaged.

Fabrizio Ravanelli to Middlesbrough

If it seems mad now to look back and recall the White Feather’s move to Boro, it must have been utterly surreal at the time. Not only was he a terrific striker in 1996, he had just won the Champions League with Juventus.

Despite joining up with Brazilians Emerson and Juninho at the north-eastern club and scoring a whopping 31 goals in one season, Ravanelli and Middlesbrough would end the season relegated to the second-tier.

Still, we’ll always have his incredible debut against Liverpool and the trademark celebration that kids reenacted on playgrounds all over the country.

Ravanelli would end up back in Italy via Marseilles, winning a Scudetto and Coppa Italia double with Lazio, before heading back to England where he joined Derby County. In another odd move, the penultimate club of his career was Dundee in Scotland, much like the next man on this list.

Claudio Caniggia to Dundee

For a club that haven’t broken their record transfer fee since 1995, Dundee somehow attracted the Argentine to join their club in 2000.

Caniggia — a World Cup runner-up in 1990 — moved to Scotland despite the fact he was fighting for a spot in the national team ahead of the tournament in 2002, making the move all the more surprising.

His talent was evident from day one, when he scored a gorgeous chipped finish on his debut.

Naturally, Rangers would end up signing him, where Caniggia won a league medal in 2003. He did make the World Cup squad after all, but in their last group game against Sweden, he was sent off after cursing at the ref from the sideline, becoming the first player to be sent off from the bench in the competition’s history.

Robinho to Man City

The transfer that changed it all. Or at least, the transfer that got the ball rolling on the change that was to follow.

While Robinho is unlikely to be hailed a City legend by the club’s fans, his arrival from Real Madrid on transfer deadline day made a statement that they were ready to upset the apple cart. Ten years on and they’ve won three Premier League titles.

The Brazillian has not had as good a time of it since, receiving a nine-year prison sentence for gang rape of a woman in Italy. His sentence is suspended while he appeals; in the meantime he plays his club football in Turkey.

David Beckham to LA Galaxy

Another game changer. Few people knew Galaxy was even a football team before Beckham left the Spanish capital for Los Angeles, but the profile of MLS has been changed ever since. The likes of Andrea Pirlo, Robbie Keane and Thierry Henry have played out their careers in the US. The former England international moved when he still plenty left to give in his career, as loan moves to AC Milan and PSG later proved.

Honourable Mentions:

Allon Simonsen to Charlton.

Julian Faubert to Real Madrid.

Gary McAllister to Liverpool.

Carlos Tevez and Javier Mascherano to West Ham.

Rob Green to Chelsea.

Diego Maradona to Napoli.

Roberto Mancini to Leicester City.

Bebe to Man United.

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