Ange Postecoglou has endured a dream start to his Tottenham reign and heads into his first north London derby with optimism as they travel to Arsenal on Sunday.
However, when it comes to Spurs managers preparing for their first outings against Arsenal the history books don’t read favourably.
No Tottenham boss in the last 20 years has won against Arsenal on their first trip across the city, with the Gunners inflicting seven defeats and dropping points on just two occasions.
Antonio Conte, Jose Mourinho and Mauricio Pochettino have all tried and failed, so can Postecoglou finally set the record straight?
Mail Sport looks back through the ages as Spurs prepare for another venture to the Emirates.
Ange Postecoglou is preparing for his first north London when Spurs travel to Arsenal on Sunday
Tottenham have started the new season strongly but an acid test against Arsenal awaits
Antonio Conte – October 2022: Loss 3-1
The Italian arrived with great expectations but succumbed to a 3-1 defeat in his first visit to the Emirates as Mikel Arteta’s side ran riot.
Harry Kane led the line but was unable to prevent another defeat as Thomas Partey opened the scoring with a strike in the 20th minute.
The Spurs talisman hauled the visitors back onto level terms before Gabriel Jesus and Granit Xhaka hammered home second-half winners.
Emerson Royal was sent off after the interval to conclude a miserable afternoon for Tottenham.
Antonio Conte arrived at Spurs with a fearsome reputation but could not avoid defeat on his first trip to the Emirates
Nuno Espirito Santo, September 2021: Loss 3-1
He only lasted 17 matches during a 124-day managerial reign at Tottenham, but one of the seven defeats Santos suffered was against arch-rivals Arsenal.
Spurs found themselves three goals down after just 34 minutes as Emile Smith-Rowe, Pierre-Emerick Aubameyang and Bukayo Saka gave Arsenal supporters bragging rights.
Current Tottenham captain Son Heung-min scored a late consolation goal as the visitors left the Emirates empty-handed after a one-sided loss.
Nuno Espirito Santo only lasted 17 matches during a 124-day managerial reign at Tottenham that included a defeat to Arsenal
Jose Mourinho, March 2021: Loss 2-1
Mourinho loves the big occasion and always knows how to rile the crowd in a derby setting, but his first outing against Arsenal failed to convince.
Tottenham arrived for a late Sunday kick-off largely tipped as favourites with the 10th-placed hosts going through a torrid period and Mikel Arteta under pressure to start getting results.
It was all going swimmingly for Mourinho as Erik Lamela netted an audacious Rabona goal to put Spurs ahead, but Martin Odegaard levelled just before half time and Alexandre Lacazette completed the turnaround from the spot in the second half.
After scoring the opening goal, Lamela went from hero to villain as he was sent off in the closing stages, ending Tottenham’s chances of a comeback.
Jose Mourinho (right) watched as his Arsenal side conceded their lead and lost to Arsenal
Mauricio Pochettino, September 2014: Draw 1-1
Once loved by Tottenham supporters, now public enemy number one after taking over at Chelsea in the summer and declaring his love for the Blues, Mauricio Pochettino was one of only two managers to salvage a point in his first away match against Arsenal.
Arsene Wenger was entering the final years of his Arsenal career and was strongly tested at home by a Tottenham side looking to get their season going after a mixed start.
Nacer Chadli put Pochettino’s young guns ahead prior to Alex Oxlade-Chamberlain equalising in the latter stages, although the match might be better remembered for nine yellow cards being dished out in a typically feisty encounter.
A fresh-faced Mauricio Pochettino avoided defeat on his first trip to Arsenal and left with a point
Andre Villas-Boas, November 2012: Loss 5-2
The Portuguese has since swapped football management for the chaos of rally car driving but was unable to stop Spurs breaking down on his first trip to Arsenal’s stomping ground.
Tottenham are no strangers to taking the lead in this fixture, and did so again here through ex-Arsenal striker Emmanuel Adebayor in the 10th minute. But just eight minutes later he was sent off, and things quickly went downhill for Spurs from there.
Arsenal opened up a 3-1 lead by half time thanks to strikes from Per Mertesacker, Lukasz Podolski and Olivier Giroud, and extended their advantage in the second half through Santi Cazorla.
Gareth Bale pulled a goal back for Tottenham, but Theo Walcott rounded off the scoring to hand Arsenal an emphatic win.
Andre Villas-Boas (middle) was unable to stop his Tottenham side from getting hit for five against Arsenal
Harry Redknapp, October 2008: Draw 4-4
Eight goals, eight goalscorers, five yellow cards and Arsene Wenger and Harry Redknapp going at one another in the dugout; this was a classic north London derby.
David Bentley’s stunning long-range volley put Tottenham in front, but Mikael Silvestre brought Arsenal level shortly before half time.
Arsenal threatened to run away with the game after the break as they twice took two-goal leads at 3-1 and 4-2, but Spurs kept fighting back.
With time running out, Jermaine Jenas scored in the 89th minute to make it 4-3, and as the game ticked into added time Aaron Lennon was on hand to tap home after Luka Modric’s deflected effort came back off the post to rescue a point for Redknapp’s men.
Tottenham players celebrate after rescuing a 4-4 draw against Arsenal in October 2008
Juande Ramos, December 2007: Loss 2-1
It was an ill-fated 12-month tenure at Spurs for Ramos, but his side actually produced a respectable performance in the run-up to Christmas as Arsenal nicked a valuable win over their cross-city rivals.
Adebayor was on the scoresheet for the Gunners this time with the serial club striker finishing with aplomb just minutes after the second half got underway.
The hosts boasted a star-studded defence featuring William Gallas, Bacary Sagna and Gael Clichy but were unable to keep out Dimitar Berbatov in the 66th minute.
Nicklas Bendtner won the match for the Gunners late on as he scored from a Cesc Fabregas corner.
Nicklas Bendtner was the unlikely hero as Arsenal inflicted a first north London defeat on Juande Ramos
Martin Jol, April 2005: Loss 1-0
An uneventful first showing against Arsenal for Martin Jol as Jose Antonio Reyes netted the only goal in a rather disappointing Highbury showdown between the two teams.
The hosts took the lead and shut up shop with Spurs failing to inspire an equaliser against an Arsenal side seeking to play catch-up against Chelsea in the race for the Premier League title.
Spurs, meanwhile, finished ninth that season as Jol struggled to get the best out of a Tottenham squad packed with upcoming talents such as Michael Carrick and Jermain Defoe.
Martin Jol’s first trip to Highbury ended in defeat in a rather uneventful north London derby
David Pleat, November 2003: Loss 2-1
Darren Anderton was the unlikely opening scorer as Pleat’s Tottenham took a surprising lead after just five minutes to stun the Highbury crowd.
However, this was Arsenal’s ‘Invincibles’ season and the Gunners – as they did so many times – clawed themselves back into proceedings through Robert Pires and Freddie Ljungberg.
The difference in quality between the two teams was startling and Spurs will be hoping for a much-improved performance when Postecgolou gets his first chance at taking down Arsenal 20 years on.
Arsenal came from behind to seal a 2-1 win against Tottenham in 2003, and then went on to wrap up the title at White Hart Lane later that season