2. Xabi Alonso
This one was well publicised. Arsenal had an incredible chance to sign Alonso and so almost did. The club no longer wanted him in their plans and instead had Gareth Barry lined up as a replacement. The Spaniard was all set to arrive at Arsenal on deadline day but as a deal for Barry fell through, so did the Alonso deal. He was on the verge of a £15million move to Arsenal and when the next summer arrived, there were bigger fish in the market for the impressive midfielder. Real Madrid signed him up and were over the moon with their purchase as he has gone on to be a vital part of their side for many years. Arsenal really needed Alonso at the point they missed out on him and fans may wonder what might have been if he did join on that deadline day years ago. Gutted Rating: 8/10
How gutted were you that Alonso didn’t join Arsenal? Comment below | Photo via Agnieszka Mieszczak