By Noah TanFollow @@Noah_Tan
Despite having secured qualification into next season's Champions League, the Gunners were largely underwhelming and eventually finished fourth, a massive 16 points behind champions Manchester United.
Premature exits from the Champions League, Capital One Cup and FA Cup to Bayern Munich, Bradford and Blackburn Rovers were not well received by the Emirates faithful, and the club hierarchy has come under fire for overseeing their eighth season without a trophy.
And Winterburn, who spent 13 season at the club, winning three Premier League titles as well as two FA Cups, highlighted the Gunners' failure to replace the likes of Robin Van Persie and Cesc Fabregas as the main reason for their trophy drought.
Speaking to FOX SPORTS at the press conference of the 5th Singapore Cricket Club Soccer Sixes 2013 competition, the 49-year-old said: "The past few seasons, especially the past two, have been frustrating and disappointing because Arsenal lost top notch players, which has made it even harder for them to compete.
"It would already have been hard enough for them to be competitive even with the likes of Van Persie, [Samir] Nasri and Fabregas within their ranks.
"Although Arsenal brought in good players, I think the quality of players that they've lost hasn't been replicated with the players they've brought in.
"But I think it might start to change from this pre-season and hopefully they'll be able to start re-strengthening."
When asked which areas of the current Arsenal squad he would like to see strengthened, Winterburn said: "When you talk about a core of the team, you talk about right through from goalkeeper, centre-half, centre-midfield and centre-forward.
"I think these are the areas Arsenal may look at to strengthen.
"They certainly need another centre-forward. I think Giroud has done okay this season, but he has really been their only option up front. If you want to be a top team, then you certainly need to have more options that what Arsenal have had, so I think they'll go for a centre-forward.
"There's a possibility that a goalkeeper might come into the squad as well. I think there will be some additions, but for me, I look at what I call the core of the team - that's what I call down the middle - as the main areas for improvement."
However, Winterburn was less forthcoming about players he thought were not pulling their weight at Arsenal.
"I don't really judge anybody; for me, it's all about how you drive yourself forward to achieve the standard you have set yourself," Winterburn added.
"Vermaelen has had a poor season, Gervinho has been inconsistent, [Jack] Wilshere has had periods where he's picked up injuries, as had [Kieran] Gibbs.
"It is unfortunate because I think if Arsenal are to get back to challenging for the title, they will have to see these types of players in top form.
"For me, it's all about Arsenal re-strengthening now and not worrying about who hasn't performed, because if you don't perform, you don't stay at the club for very long."
While the playmaker Santi Cazorla and defender Laurent Koscielny has both earned acclaim for their eye-catching performances, Winterburn refused to single out a particular player as the Gunners' best this season.
"I don't think there's been one Arsenal player who has been outstanding for the whole season," Winterburn mused.
"Cazorla has had periods where he's been very good for Arsenal. Koscielny has done well again, while Wilshere had a little period after he came back from his injury where he was playing really well.
"There's been two to three, maybe four players who have had little periods where they've done well before somebody else takes over.
"So I don't think there's one player who has been consistent enough, and that's been Arsenal problem.
"It's been a difficult season for them.
"Their consistency, particularly since Christmas has been impressive, while their inconsistency before Christmas was obviously rather worrying.
"For me, success is about winning things as a player, and unfortunately for Arsenal, they haven't been consistent enough to do that for the last eight seasons."
Arsenal have been linked with a slew of players this summer, with the likes of Gonzalo Higuain, Stevan Jovetic and Victor Wanyama believed to be high on the club's shopping list.