Cristian Romero's own goal put the Gunners in front before Son Heung-Min scored the first of two goals, netting smartly from Maddison's cutback. Bukayo Saka then scored a 54th-minute penalty -- awarded for handball by Romero on VAR review -- only for Tottenham to equalise a minute later as Son finished again from another Maddison pass.
Prior to Ange Postecoglou's appointment as head coach this summer, the club has long been dubbed "Spursy" by their critics, a dig at their propensity to collapse in difficult situations or with silverware in sight: Tottenham have not won a trophy since 2008.
But after extending their record under Postecoglou to four wins and two draws in six Premier League games, Maddison highlighted Spurs' resolve in also coming from a goal down to beat Sheffield United last weekend.
He told TalkSport: "When you hear fans and neutrals talk about Tottenham, they often say 'soft, weak, bottle it, Spursy, all that rubbish.' I think the last couple of weeks shows we might be going in a slightly different direction because we scored in the 98th and 101st minute against Sheffield United to win late on when it looked like it was going to be one of those days.
"And today we go behind twice at arguably one of the best teams in the world and we pull it back and we're still fighting to the end."
Postecoglou was left to bemoan what he believes is ongoing confusion around the handball rule after Romero was punished once referee Robert Jones was sent to the monitor.
"Any clarity would be good," Spurs' coach said. "I've got no idea. That's just with me, I don't know. I've got no idea what the handball rule is because I've seen all sorts of handballs given and I've seen all sorts not given and they look identical to me. So I don't understand.
"I saw the one yesterday at Wolves and it just seems if it hits your hand it's a penalty and then other times if it hits your hand, it isn't a penalty. I've got no idea. It is the one rule in the game I just don't understand.
"Unless we start developing armless defenders, I don't know how you are supposed to block things and be in a natural position. It is what it is.
"You kind of hope these things even themselves out over the course of a year, but I don't understand the handball rule. I have said that to referees in the past and I don't know how they see it to be honest."