Tuesday's Carling Cup semi-final second leg will be the 16th encounter between the north London rivals in cup competitions.
Gascoigne scored one of the finest FA Cup goals in the 1991 semi
The teams drew 1-1 at the Emirates Stadium and Arsenal have not been beaten in the fixture since November 1999 but Spurs have registered some famous victories over their neighbours in the past.
BBC Sport takes a look at their previous cup clashes...
FA Cup 3rd round, Jan 1949 - Arsenal 3-0 Tottenham
Second Division Spurs were managed by former Gunners winger Joe Hulme, while Arsenal were the reigning league champions.
The gulf in class showed as the hosts eased to victory thanks to goals from Ian McPherson, Don Roper and Doug Lishman.
Arsenal lost in the next round to Derby and finished fifth in the league, nine points behind winners Portsmouth, while Spurs were promoted to the top flight the following season.
League Cup semi-final Nov/Dec 1968 -
Arsenal 1-0 Tottenham; Tottenham 1-1 Arsenal
John Radford grabbed a late winner for Arsenal in the first leg.
And in a niggly second match Jimmy Greaves brought Spurs level overall, only for Radford to head the winner.
Arsenal went on to lose 3-1 to Swindon in the final.
League Cup 4th round, Nov 1980 - Tottenham 1-0 Arsenal
Argentina star Ossie Ardiles slotted in the only goal after Garth Crooks' effort was saved to earn progress for a Spurs side who were becoming serious cup contenders under Keith Burkinshaw.
They were knocked out in the next round by West Ham but celebrated FA Cup glory six months later when they beat Manchester City in a replay in which Ardiles' countryman Ricky Villa scored a sensational winner.
FA Cup 3rd round, Jan 1982 - Tottenham 1-0 Arsenal
A rare howler from Arsenal keeper Pat Jennings, who allowed a Garth Crooks shot to squirm under his body, handed his former club victory.
Spurs were chasing silverware on several fronts but lost in the League Cup final to Liverpool and the Cup Winners' Cup semi-final to Barcelona before finishing on a high by winning the FA Cup thanks to a Glenn Hoddle penalty in the replay against QPR.
League Cup 3rd round, Nov 1983 - Tottenham 1-2 Arsenal
Charlie Nicholas, who had been going through a lean patch, put Arsenal ahead after an error from Spurs keeper Ray Clemence and Tony Woodcook hammered in a second before Glenn Hoddle pulled one back from the spot.
Arsenal lost in the next round at home to Walsall and manager Terry Neill was sacked soon after.
League Cup semi-final, Feb/Mar 1987 - Arsenal 0-1 Tottenham; Tottenham 1-2 Arsenal; Tottenham 1-2 Arsenal
Clive Allen forced home from close range to give Spurs an advantage and the prolific striker - who ended the season with 49 goals - put his team in control with another in the second leg.
But Viv Anderson headed one back and Niall Quinn stabbed in the equaliser to force extra-time, which could not separate the teams and a replay was needed with away goals not counting.
Allen again put Spurs ahead at White Hart Lane but substitute Ian Allinson and teenager David Rocastle scored in the last 10 minutes to snatch victory.
Charlie Nicholas netted twice in the final against Liverpool to give George Graham his first trophy as Gunners boss, while Spurs were stunned in the FA Cup final by underdogs Coventry.
FA Cup semi-final, Apr 1991 - Tottenham 3-1 Arsenal
Wembley hosted a semi-final for the first time and was witness to one of the greatest goals in FA Cup history.
With the game a few minutes old, Paul Gascoigne fired in a magnificent free-kick from 35 yards and Gary Lineker tapped in a second.
Alan Smith headed one back but Lineker made the game safe with a third that David Seaman should have saved.
Spurs won the final against Nottingham Forest but Gascoigne suffered a serious knee injury making a reckless tackle on Gary Charles.
FA Cup semi-final, Apr 1993 - Arsenal 1-0 Tottenham
This was not a Wembley classic by any stretch of the imagination.
Arsenal, a well-drilled machine in the cup competitions under George Graham, won a niggly affair thanks to a Tony Adams header from Paul Merson's free-kick.
The Gunners triumphed in the final, as they had in the League Cup by grinding down the same opponents, Sheffield Wednesday.
FA Cup semi-final, Apr 2001 - Arsenal 2-1 Tottenham
Arsenal were now a much more attractive proposition under Arsene Wenger - and clearly the dominant force in north London.
Spurs took a surprise lead at Old Trafford through Gary Doherty's header but Arsenal's overwhelming superiority was rewarded through strikes from Patrick Vieira and Robert Pires.
Injury cut short Sol Campbell's last game for Tottenham before he caused a furore by joining Arsenal, who lost in the final to Liverpool despite again dominating.
League Cup semi-final, Jan 2007 -
Tottenham 2-2 Arsenal; Arsenal 3-1 Tottenham
Spurs took a two-goal lead in the first leg through Dimitar Berbatov and an own-goal by Julio Baptista.
But Arsenal's youngsters roared back after the interval and Baptista grabbed a brace to send the teams to Ashburton Grove on level terms.
Emmanuel Adebayor put Arsenal ahead there and though Mido levelled against the run of play, Jeremie Aliadiere and a Pascal Chimbonda own-goal sent Arsenal through to Cardiff, where they lost to Chelsea.