However close they appear to be showing signs of ending their barren run, another player is guaranteed to add to the list, and become the 24th ex-Arsenal player to win a major trophy since 2005, with a combined 56 medals already won to date.
Let's get down to specifics: Flamengo take on Atletico Paranaense in the Brazilian Cup Final this Wednesday night.
In Arsenal terms, that pits Flamengo's Andre Santos up against Paranaense's Fran Merida.
Both left the Gunners in different years and under contrasting circumstances. Santos left this summer, having been loaned to Gremio in February, he could not have been ushered out of the door quick enough this summer, sold to Flamengo.
The 30-year-old left-back has played 19 league games since arriving, with two goals and two assists, and has regularly been picked in midfield rather than defence, and is on the fringes of the national team.
Merida has had it far tougher. He signed after exhausting his welcome at Spanish second division side Hercules in January. Arsenal had tried to keep him in 2010 but he took a punt on a return to Spain with Atletico Madrid which did not pan out.
Despite signing early in 2013, he did not convince his coaches, and was only handed his debut in September, one he marked with an excellent goal - against tonight's opponents Flamengo. He is now ingratiated with the first team, but is likely to start the final on the bench, unlike Santos who is expected to be picked from the kick-off.
Neither players have won any silverware since leaving the Gunners, and this will be a real chance for them to enjoy some success.
Flamengo sit 11th in the league, winning their first game out of the last four at the weekend, with Paranaense are as high as third.
The game begins at 11.50pm UK time, and it promises to be quite a contest.
image: © Ronnie Macdonald