Victories over the Gunners in the past decade or so have been few and far between for Spurs and subsequently much more memorable.
However, Mauricio Pochettino's side are astonishingly now being labelled as favourites.
Off to Wembley
With Tottenham on the verge of their first visit to New Wembley in 2007, it was Arsenal that stood in their way in a semi-final clash at White Hart Lane.
Jermaine Jenas, who was known amongst Tottenham fans as not particularly setting the pitch alight throughout the season - scored the opener. However, when the NLD came around he was like a different player - often grabbing himself a goal.
Jenas scored the opener in what proved to be an unexpected convincing win over their bitter rivals. The Lilywhite's went on to score another three goals - putting them four goals to the good.
A late Emanuel Adebayor strike was too late to provide the visitors a chance as Steed Malbranque's 90th-minute goal regained Tottenham's four-goal advantage.
An incredible victory for Juande Ramos' side over their rivals from down the road. This saw Spurs beat Arsenal for the first time in all competitions since 1999 - Spurs also went on to beat London rivals Chelsea in the final to lift the Carling Cup at Wembley.
Kaboul completes comeback
It was 17 years since Spurs had managed a win away to Arsenal and with the Lilywhite's 2-0 already at half-time, it looked set to be made 18 years.
However, the stern words of manager Harry Redknapp must have sunk home as Tottenham came out for the second-half looking like a completely different team.
Gareth Bale started the comeback, only five minutes into the second period as he slotted home with his left foot. Just over 10 minutes later, Spurs were awarded a penalty - which fan favourite, Rafael van der Vaart stepped up to take.
The Dutch international slammed the penalty home and Spurs were level after being two goals down. However, they were not finished there.
Van der Vaart whipped in a free kick with only five minutes of normal time left on the clock. Defender Younes Kaboul rose above the rest and his glancing header was enough to beat the hosts' goalkeeper Lukasz Fabianski.
To the disbelief of everyone in the stadium, after being dominated for the entire first half - Tottenham had done it. They had somehow managed to turn around the two-goal deficit and take all three points back home to the Lane. However, the victory had more weight to it than just the three points it gave Tottenham a new found belief for the rest of the season.
Last derby at the Lane
It was an emotional day for many, the last ever north London derby at White Hart Lane. There was more on the line this time around than the normal bragging rights - if Arsenal were to win, it would never be forgotten.
It was a must-win game for the Lilywhite's - still chasing Chelsea for the title and the notion that a win would confirm that they would finish ahead of their arch-rivals for the first time in 22 years.
Going into the game, Spurs were soaring and Arsenal looked to be in a crisis. Tottenham showed their superior form over Arsenal as goals from Dele Alli and Harry Kane proved to be the difference. It was a derby different to what many Spurs fans were used to. Tottenham completely dominated from the whistle.
It could and probably should have been more than just the two goals difference. Regardless, Spurs were a level above Arsenal in all departments and it certainly showed on the pitch - Tottenham looked to have wanted it more than the visitors.
Arsenal fans have had many happy memories at Tottenham's old home over the years. Therefore, it was crucial that Tottenham won and did not allow them to enjoy another one - a game that proved the shift of power in north London?