VIDEO: The best and worst from past transfer windows

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As deadline day of the January transfer window approaches us, the NBC Sports soccer crew is breaking down some of the biggest transfers in Premier League history.

[ DONE DEAL: Juan Cuadrado finalizes move to Chelsea ]

Middlesbrough may still be celebrating their historic win over Manchester City, but Boro fans would like to forget the arrival of Afonso Alves in 2008. The club paid nearly $26 million for the Brazilian striker, only to see his production plummet as the striker was out of the Premier League in under two seasons.

Who could forget Fernando Torres’ record-breaking move from Liverpool to Chelsea? After shelling out $75 million for the Spanish striker, Torres went from one of the most feared goal-scorers in the world to an often unused substitute off the bench. This move came in January of 2011, and Torres has yet to regain his form.

[ RELATED: Sunday’s Transfer Rumor roundup ]

But the January transfer window isn’t just all blunders, as players such as Rio Ferdinand and Frank Lampard left for massive clubs, kickstarting legendary careers for two of England’s best players of this generation.

Arsenal shelled out $12 million for Dennis Bergkamp, a massive fee back in 1995, in a move the Gunners wouldn’t regret as the Dutchman helped lead Arsenal to three Premier League titles and four FA Cup wins. He now has a statue in his honor outside of The Emirates.

With the transfer window closing tomorrow, what deals could go down in history? Is Wilfried Bony’s move to Manchester City the key piece to catching Chelsea? Is Juan Cuadrado the final piece in Mourinho’s master plan?

Only time will tell.