Tottenham Hotspur's win over Manchester City means it can jump ahead of its bitter rival on Saturday afternoon (Sunday morning AEST) if it beats Wigan Athletic at the
Although Arsenal entertains Manchester United a little over 24 hours later, it is still favourite to land a top-four finish which will boost the coffers ahead of what promises to be a crucial close season for the Gunners.
Arsenal fans yearn for a big-money signing every transfer window after watching the likes of
But the low wage ceiling at the club means it will not be able to compete with most of its rivals in the market, Winterburn says.
"The problem at Arsenal is always that they have a wage structure which is fairly high, but in terms of competing with Manchester United, Manchester City and Chelsea, if they are after the same player, particularly with the history of Man Utd and Chelsea of late, the player is more likely to go to one of those teams."
The Gunners have been in good form of late, dropping just two points from their last seven games, but Winterburn still thinks major surgery needs to be done to the Gunners squad if they are to compete for a top-four finish again next season.
"They will look down the spine of the team to strengthen," said the former Arsenal left-back.
"They will possibly be looking at a goalkeeper, maybe another centre-half, another centre forward to help out
"There are a few squad that haven't been involved hardly and they might move on.
"Looking at Arsene Wenger's history of buying players he doesn't really go for the big established £30 million players. Around £15 million is probably his maximum spend so it will be quite interesting to see what he does. I think they need strengthening."
Despite Tottenham's win, Arsenal and Chelsea are still in pole position to take up the final two Champions League qualification spots.
Winterburn, who played 584 times for Arsenal during a trophy-laden 13-year spell, thinks there are plenty of twists and turns to come before the season ends.
"It will probably go to the last game," the former defender said.
"All three teams will drop points. It's so hard to predict what is going to happen. It's going to be very close.
"Even if Arsenal go behind Spurs they know that those two teams have got to play each other before the end of the season so they will still believe they have a fantastic chance of then getting to third or fourth."
English Premier League
Jordan Henderson believes Daniel Sturridge's availability to play against Chelsea would be "massive" for Liverpool.