Even with a title drought extending to a dozen years, back to the unbeaten "Invincibles" team of 2004, the Gunners have won the league on 13 occasions. Tottenham, meanwhile, claimed the last of its two league crowns in 1961.
The last time Tottenham finished ahead of Arsenal in England's top division was in 1995, in the infancy of the Premier League era.
As much as derby games pique the interest of their supporters, playing for silverware and landing in the Champions League are more commonplace scenarios for the red half of North London.
But in this strangest of Premier League campaigns, could Spurs turn the tables and, for once, get the better of their more esteemed neighbors?
It is looking increasingly likely, and Saturday's 183rd North London derby at White Hart Lane could give Tottenham a substantial boost in its bid to snap a 55-year title drought -- while also realistically killing off Arsenal's hopes.
"If you asked me at the start of this football season whether Spurs would win the championship, the Premier League, I would have said we would have as much chance as Donald Trump becoming president," former Tottenham chairman Alan Sugar tells CNN. "And two phenomena have happened, really."
With both teams still in the title race for now -- second-place Tottenham has 54 points, three behind leaders Leicester City, with Arsenal third on 51 -- one can say this is the most pivotal North London derby in decades.
"It's probably one of the biggest games in England -- the world, even -- and for us both to be up there fighting at the top of the table just makes it even bigger and even more special," Tottenham midfielder Dele Alli tells the club website
Arsenal's longstanding manager, Arsene Wenger, should take comfort in knowing that his side -- if a loss does come Saturday -- will probably still qualify for the Champions League. After all that is, for the Frenchman, like winning a trophy
However, Arsenal fans, who pay the highest season ticket prices in England
, want more. With Chelsea and Manchester United effectively out of the title reckoning and Manchester City firm outsiders, those fans could be forgiven for thinking that this should be the season when Arsenal trumps the trio of massive spenders and everyone else.
The time is now for Arsenal, since Chelsea, Manchester United and Manchester City all figure to be improved next season. United is continually being linked with Jose Mourinho, still one of the most successful managers ever despite his blip this season with Chelsea
, while Pep Guardiola will be patrolling City's touchline
Wenger's men led the Premier League by two points on January 12th but have stumbled in a scenario that is not unusual for them come February or March.
With only two wins since the middle of January, the same questions are surfacing: Does Arsenal have the requisite mental strength to win the title? Is it time for Wenger to go?
"You're fired!" is a phrase synonymous with Sugar on his popular UK television show "The Apprentice," and calls for Wenger to depart have picked up steam since the start of the 2013-14 season -- when chants of "Wenger out" became noticeable at Emirates Stadium.
Yet his past success and achievement in keeping Arsenal financially sound lead many to believe the 66-year-old will stay in charge for as long as he wants.
Graeme Souness, a former Liverpool manager, claimed Arsenal bordered on being a "joke"
in its 3-2 loss at Manchester United last Sunday.
United's hero that day was an 18-year-old making his Premier League debut, Marcus Rashford
, and of the Red Devils on the field at the final whistle, six were under the age of 23. United's kids beat Arsenal's more experienced internationals.
Arsenal then slumped to a third straight defeat in all competitions, 2-1 at home to relegation-threatened Swansea, Wednesday.
"There's a word I want to use -- but I can't -- which describes a lack of something that real players have and this Arsenal lack it in abundance ..." Souness said in his role as a pundit for Sky Sports.
"I'll stand on my head if they prove me wrong and go and win this league ..."
Even Arsenal forward Alexis Sanchez, out of form since returning from a hamstring injury, questioned his team's hunger
ahead of the derby.
Scathing remarks about Spurs have been far less frequent, irrespective of the 1-0 loss at West Ham, also Wednesday, that snapped a six-match league winning streak.
The current climate also means this could be Tottenham's time to grab the bull by the horns but, given the progress made under Argentine manager Mauricio Pochettino, much more than fleeting success is a possibility.
Wenger revolutionized training methods when he joined the Premier League in 1996 and Pochettino's own training regimens have drawn attention, with their double sessions and a grueling preseason program.
But Tottenham's up-tempo pressing game shows little sign of waning. Pochettino has also blended youth with experience, notably unearthing Alli.
Tottenham possesses the stingiest defense in the division -- just 22 goals conceded -- and at the other end of the pitch, boasts Harry Kane, the league's third-highest scorer with 16 goals. The consistent Kane is a contrast to Arsenal's hot-and-cold striker, Olivier Giroud.
Although Giroud has netted 12 times, the Frenchman is scoreless in his last 10 matches.
Wenger will be without the services of standout keeper Petr Cech on Saturday, meaning David Ospina deputizes.
And on the subject of saves, Arsenal likely needs victory to save its season.