Fans may say it took too long in either case, but once this summer came around Arsenal could not move on a pair of Brazilians quickly enough.
Santos was sold for a fraction of the £6.2 million Arsenal paid for him, moving to Flamengo, while Denilson was released from his contract a year early and made a free agent, where he signed for Sao Paolo.
The two Arsenal outcasts came face to face with one another with their respective teams this week, and both were selected as starters.
So who came out on top?
The winner was Denilson's Sao Paulo side, who came out 2-0 victors. It was a chastening experience for Flamengo who as a results slipped from 10th to 12th in the table while the winners stayed eighth.
Andre Santos had a tough game, the only defender to make just one tackle, and was one of just three defenders on the pitch to be dispossessed twice or more.
He was also booked late in the first half, ensuring he had to be increasingly careful as the game progressed, but he was able to showcase his attacking qualities, creating two goalscoring chances, which were wasted by his teammates.
Denilson was also booked in the closing stages of the match, but after a man-of-the-match display. The 25-year-old made five tackles and seven interceptions as he dominated the midfield.
Playing alongside one-time Brazil internationals Ganso and Luis Fabiano, the former Arsenal man has a simple task of acting as a midfield spoiler and letting the more creative players do the damage, and it certainly worked.
Andre Santos has a chance to win a trophy in Brazil, into the domestic cup final at the end of the month, where he faces Atletico Paranaense - who boast another ex-Gunner in Fran Merida. He will hope that time he has more success.
image: © Ronnie Macdonald