If things had worked out differently, Cristiano Ronaldo could have signed for Arsenal. The Gunners were keeping tabs on the Portuguese as a youngster, but little did they know that he would go on to become one of the greatest players of all time.
Instead of playing for them, Ronaldo has haunted Arsenal on a few occasions, scoring nine goals in 18 games against the Gunners. Ronaldo's most memorable appearance against the north London club was in the second leg of the Champions League semi-final in the 2008/09 season, where he scored twice and claimed an assist in a 3-1 win for Manchester United at the Emirates Stadium to knock Arsenal out of the competition.
Six years before, the Gunners were one of the clubs rivalling Man United for Ronaldo's signature, with the winger impressing at Sporting Lisbon. However, the Red Devils acted quicker than Arsenal, with Ronaldo becoming the most expensive teenager in English football history as he put pen to paper on a contract at Old Trafford.
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"I was asked by our chief scout if I would go with him to see a young boy playing for Portugal Under-18s, and he was only 16," former Arsenal vice-chairman David Dein told Sky Sports News.
"You can imagine who that young guy was. It was Cristiano Ronaldo. The following day Manchester United came and blew us out the water. These things happen."
Failing to sign Ronaldo isn't the only regret Dein has when looking back on his time at Arsenal. He has also revealed his frustration at letting Ashley Cole controversially join Chelsea in 2006, saying that the club did not do enough to keep him.
"It really was a great shame because Ashley was home-grown, an Arsenal boy, and I regret that we didn't do enough at the time to keep him at the club," said Dein.
"It was also at a time where we were talking about building the stadium and finances, so tensions were raging about how we were going to finance the stadium and we were watching every penny.
"We didn't go enough to keep him, and I regret that with hindsight. Ashley, if you're listening, I'm sorry."
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