7. Robin van Persie (Arsenal to Manchester United)
After Robin van Persie had one of his best seasons in an Arsenal shirt with a 30 goal return, he went onto completely shock the football world by refusing to sign an extension.
With just a year left on his contract, the Gunners were forced to sell their talisman in 2012. To make matters worse it was to their rival Manchester United – who Van Persie guided to a Premier League title the following year.
6. Robinho (Real Madrid to Manchester City)
Robinho had plenty of options after he rejected a new contract with Real Madrid having gained a strong reputation, and while the deal didn’t work out great for Manchester City it was a big transfer for them back when the deal was done in 2008.
City had just been taken over by the Abu Dhabi United Group and as a statement of intent their first piece of business was the £32.5m purchase of the Brazilian whose form had begun to dip which left the Real bosses laughing.
5. Carlos Tevez (Boca Juniors to Shanghai Shenhua)
Carlos Tevez could easily fill the majority of the list and while his move to Manchester City from West Ham had fans puzzled, moving to Chinese Super League side Shanghai Shenhua left people perplexed, mainly because they didn’t know about the league.
The Chinese teams have been stealing talent all over the world in the last two seasons and the staggering £71.6m they paid for the 33-year-old was jaw dropping.
To make matters more so laughable, Tevez, who joined his boyhood club Boca Juniors and had planned to retire there, was once quoted saying: “Football is only about money, and I don’t like it.” Shanghai Shenhua certainly changed that.
4. Michael Owen (Newcastle United to Manchester United)
Michael Owen’s 2009 move to Manchester United from Newcastle simply left fans shocked and confused. Of course he had proven himself as one of the world’s best strikers, but at 30 he was clearly seeing out his career so why would a top club want him?
United may have just wanted to bolster the team, but with just five goals during his three year stint at Old Trafford it was an unsuccessful step back to the top.
3. Julien Faubert (West Ham United to Real Madrid)
Julien Faubert’s 2009 loan move to Real Madrid had left shock waves, which can still be felt to this day.
After a poor season with West Ham the previous year nobody could work out why the La Liga giants wanted to bring him to the Bernabéu, even on loan.
That question wasn’t answered after he only made two league appearances his only contribution was falling asleep on the bench!
2. Oscar (Chelsea to Shanghai SIPG)
Chelsea star midfielder Oscar was becoming frustrated at the club and while a transfer request was looming fans were shocked when he too decided to move to the CSL and Shanghai SIPG in January 2017.
The other stars are seeing out their careers, but in-form Oscar had plenty of other options before accepting the £60m move, leaving fans confused as he opted for the unknown league.
1. Tevez & Mascherano (Media Sports Investments/Corinthians to West Ham)
Easily one of the most shocking transfers in history and for a number of reasons. The first being two quality players who impressed during the 2006 World Cup joining West Ham among the vast amount of interest from some of Europe’s top clubs.
And the second being the scandal that followed after Media Sports Investments’ third party ownership was revealed. Both players left after a year, but their contribution kept the Hammers in the Premier League.