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#6 Jonathan Woodgate to Real Madrid (2004)
Jonathan Woodgate's stint at Real Madrid was an unmitigated disaster.
Despite being injured at the time, the English centre-back was signed from Middlesbrough in the summer of 2004. But Woodgate took an entire year before making his Real Madrid debut, which turned out to be a disastrous one, much like his stint at the club.
He scored at the wrong end and then got sent off for two bookable offences in quick succession. After waiting 13 months for his first game, Woodgate lasted only 66 minutes on the field.
Though he did score at the right end later that season, Woodgate played only nine games for Real Madrid before he returned to English football.
He would later talk about his 'regret' at Real Madrid, saying:
“It was great! I loved it. Hadn’t played for a year. First game: red card and an own goal. It’s no problem. When I played, I played well. I played good games when I played, but I didn’t play enough. That’s my biggest regret. I always think about it. I was at the biggest team in the world and I couldn’t play every game.”
#5 Sol Campbell to Notts County (2009)
Two-time Premier League winner Sol Campbell decided to take a route less traversed to wind down his illustrious career.
After rejecting offers from a plethora of Premier League teams, Campbell signed up with fourth-division Notts County at the end of the 2008-09 season in a move that beggared belief.
Arriving on a lucrative £40,000-a-week contract - more than that of any League Two player at the time - Campbell asserted that he was not moving there for financial reasons.
However, after the club's jerseys and merchandise sales went through the roof with the news of the arrival of Campbell, the player only played one match.
Woefully short on match fitness, the decorated former Arsenal defender huffed and puffed his way around before terminating his contract by mutual consent a month later.
#4 Alexis Sanchez to Manchester United (2018)
Alexis Sanchez arrived at Manchester United to much fanfare in January 2018.
However, the Chilean player had a torrid time at Old Trafford after apparently leaving behind his scoring boots at Arsenal.
Tallying a meagre five goals and nine assists in 45 games in all competitions, Sanchez was a pale shadow of the player who lit up the Emirates Stadium with his energetic performances. The player's gargantuan wages also didn't help his cause, as the club faithful felt that Sanchez was not giving it his all despite earning the big bucks.
Sanchez's calamitous stint at Old Trafford came to an end in the summer of 2019 when he joined Inter Milan. He has fared slightly better for the Serie A league leaders, scoring nine goals and assisting 17 times in 60 games.
