Spurs have failed to place higher than Arsenal in every top-flight campaign since 1994-95, but the London rivals are again tightly matched this time around having only been separated by one point last time out.
Tottenham sit second, three points clear of Arsene Wenger's fourth-placed side, who have one game in hand.
"It is very feasible [that Tottenham finish above Arsenal]," Gunners icon Wilson, speaking ahead of the London Football Awards, told Omnisport.
"I think I can just about bear one year in 20 for Spurs to finish ahead of Arsenal and I am sort of preparing myself for that.
"As for the manager Mauricio Pochettino, what he has done since he has been there – he showed it at Southampton to a degree – I think he has great ideas.
"I have heard of certain things he makes the players do at the training ground, I am all for little initiatives that make it different. He has got himself a squad of players who have got a lot of youth on their side."
But Wilson thinks that is another run that could well come to an end for his old club Arsenal's main rivals, with Spurs joining Wenger's side in the last eight of the FA Cup.
"They will pick up a trophy this year at the back of my mind," he said.
"I thought they would probably at least be knocking on the door again as the season came to a close.
"And they may well do, who is to say they won't now having been out of Europe. They are in two competitions – still in the FA Cup and they can have a big say in the title race as well."