Things haven't gone to plan this season for either of the north London rivals, with Spurs seventh and the Gunners ninth in the Premier League.
Overhauls are desperately needed for both sides while doubts remain about the future of Harry Kane at Tottenham.
But, which club is in a better position? Former Spurs midfielder O'Hara made his case for his old club.
That didn't go down too well with Arsenal fans and Julian the Gooner called in to Thursday's talkSPORT Breakfast to challenge O'Hara on his verdict.
No punches were pulled in this brilliant exchange as the pair went toe-to-toe live on air.
Julian the Arsenal fan said: "Tottenham are a year behind Arsenal. That's their best outcome. They need a new manager, need a new defence and midfield. They are about to lose their striker.
"Arsenal, they've got Arteta in and okay he's not Pep Guardiola, but he's decent and Tottenham aren't about to go and get Allegri are they?"
O'Hara said: "You're not going to spend more than Spurs. That's not going to happen. You know that's not going to happen.
"All your fans hate the owners. All I constantly see on Twitter is Kroenke out. He's not going to spend lots of money.
"Mikel Arteta was assistant manager to Pep Guardiola and has got the Arsenal job. You're ninth in the table.
"You're best player is Aubameyang and he hung his boots up this season after he signed a contract for £350,000-a-week.
"You can't say you're in front of Spurs because you finish behind us every season."
Julian said: "We've had a terrible, terrible season, I'll give you that. Aubameyang, nobody would have foreseen that.
O'Hara argued: "But we've had a terrible season as well."
Julian replied: "You've got to start the clear-out. At best, you're a year behind. You've got to do this summer what we've been doing for a while."
O'Hara interjected and said: "Disagree with that. We can do it this summer, but Arsenal don't do it. They're pretenders.
"Arsenal haven't been a big club for eight years. When was the last time you got Champions League football?
"Arsenal win the FA Cup, well done. When was the last time you got in the Champions League?"
Julian added: "We might get into Europe this summer. That's 26 years in Europe. That would be 26 years in Europe.
"The best thing you can do is try and get Wenger out of retirement, that's your best bet. He's the only chance you've got of getting into Europe next season, Jamie."
O'Hara continued to be challenged on his views with another fan calling in for a debate with the ex-Tottenham man, but was told to 'bore off'.
And the talkSPORT pundit reiterated his views that Spurs are in a better position than Arsenal, despite the Gunners' uptick in form.
Since Boxing Day, only Man City have won more points (57) than Mikel Arteta's side (44). Spurs have won just 34 points since then.
Premier League table since Boxing Day
Man City - 57 points
Arsenal - 44 points
Man United - 42 points
Chelsea - 42 points
West Ham - 41 points
Leeds - 39 points
Leicester - 39 points
Liverpool - 35 points
Tottenham - 34 points
Everton - 33 points
Brighton - 29 points
Aston Villa - 27 points
Burnley - 26 points
Crystal Palace - 26 points
Wolves - 25 points
Newcastle - 24 points
West Brom - 19 points
Southampton - 19 points
Fulham - 18 points
Sheffield United - 18 points
On the reasons why he thinks Tottenham are in a better position, O'Hara added: "All I'm saying is I think Spurs are in a better position because I think they've got a better squad, they've got more going for them, they finish above Arsenal every season, they've got a better stadium, better training facilities and are a better football club.
"We were in the Champions League two seasons ago. We had a poor season and we are still above Arsenal.
"If we win against Leicester we finish above Arsenal. We'll be in the Europa League and Arsenal aren't going to be in the Europa League, so we're in a better position."