Wright, who turns 50 in November, participated in his fair share of all-North London fixtures during seven prolific years as a Gunner during the 1990s.
And ahead of Sunday's much-anticipated Premier League clash at the Emirates Stadium, he emerged victorious from another - sort of.
At the launch of Vodafone's new 4G network, Arsenal legends Wright and Tony Adams took on Tottenham alumni Ledley King and Les Ferdinand in a penalty shoot-out, where each man's spot-kicks were measured on speed as well as accuracy.
And though 'Wrighty' is hopeful his old side can stick it to their rivals for the second time in the week, he admitted it will be difficult to predict what kind of Tottenham performance to expect.
He was, however, confident of one thing: goals. And plenty of them.
"We’ve been in Trafalgar Square, seeing how fast we can kick a ball to promote the speed of Vodafone’s 4G," he explained to Eurosport-Yahoo!.
"To be honest, though, the game is going to be very tough to call. Both sides like to attack so I see plenty of goals. A 2-2 draw is not a bad bet.
"Spurs will be really up for this particular derby as they have a lot of talented new signings who will be positively buzzing once they take in the atmosphere of the fixture for the first time.
"When I started at Arsenal, that first North London derby was amazing. Absolutely brilliant. I can only imagine that feeling will be running through most of the Tottenham new boys.
"It doesn’t make me too concerned from an Arsenal standpoint, though. It remains to be seen if the new recruits turn out to be great business, though of course the potential is there."
While it's hard to deny that Andre Villas-Boas has put the money set to come into the club courtesy of Gareth Bale's impending record transfer to Real Madrid to good use with the arrivals of Paulinho, Roberto Soldado, Erik Lamela, Christian Eriksen, Vlad Chiriches and others, Wright feels it will not be that straightforward replacing someone as talismanic as the Welsh wizard.
"The profit from selling Gareth Bale to Real Madrid will be fantastic business for Spurs," Wright explained, "but there is no denying how important he was to the team last season and that hole will take more than a few great signings to fill in the short term.
"Many will see Arsenal as ripe for the picking in such a big match, and yes all the talk of a ‘war chest’ not coming to pass and losing to Aston Villa on opening day both hurt a lot.
"But there was a lot to take from the last three games, beating Fenerbahce twice and Fulham. Of course they weren’t the toughest games they will play, but they got through it with a young, thin squad and it was a positive sign that they are dealing with pressure of not recruiting in bulk.
"Even if Arsenal lose to Tottenham, heaven forbid, I feel it is early enough for them to bounce back from with less fallout than if the game was in the thick of the season."
And Wright has one more message for the Gunners faithful: have faith that a big signing will indeed come the club's way before Tuesday, when the window will be closed.
He said: "There’s still a bit of time left in the window for Arsenal to add a couple of bodies, and for all we know the money mooted at the start of the summer is still there to be spent.
"I know Arsene Wenger has been frugal about his bids so far but with so many first-team injuries – and Lukas Podolski joining the list recently – I think that might persuade him to nip in before the deadline with a bit more determination to close a few deals.
"The thing most Arsenal fans will be wary of in that scenario is the club making ‘panic buys’ as the clock ticks, but I have faith in Wenger and the board that they will make sensible enquiries even on deadline day.
"I really think there still are quality players available for the right money, too. If I were in charge, my first targets would be Mesut Ozil and Juan Mata.
"There’s no guaranteeing that either will leave Real Madrid or Chelsea by Tuesday, but with Chelsea recruiting more forwards and Bale arriving at Real Madrid, a club could definitely test their resolve with a good bid.
"Mata or Ozil would make any team more dangerous than they already are and they are both the sort of signing that would ease Arsenal fans’ nerves for the season ahead."
Vodafone kicks off 4G network in London before launching in 12 more cities before the end of the year. For more information visit www.vodafone.co.uk/4G