Sunday's Premier League fixture at Stamford Bridge brings together two clubs from the same city but with very different prospects.
Arsenal, the visitors, are in the midst of a malaise that is coinciding with a bright new era at Chelsea under an exciting manager in Antonio Conte who keeps his side moving forward as their rivals go backwards.
The Blues have had their ups and downs since becoming the first - and still only - London club to win the Champions League, in 2012, but the Gunners have been in a steady decline ever since reaching the final in 2006.
The fact that Chelsea are back in the tournament this season whereas Arsenal are out, for the first time since Wenger took charge, merely serves to highlight the growing divide between the two teams.
Arsenal's last league title was 13 years ago, with the team having gone from invincible to self-destructive. A club that once had designs on being the best in Europe is no longer among the top four in England. Indeed, the Gunners finished fifth last term, a staggering 18 points behind champions Chelsea.
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Unfortunately for the Gunners' disgruntled fans, they are destined for more disappointment this season - despite a decent transfer window: club-record signing Alexandre Lacazette already looks like he can hit the back of the net consistently, while Sead Kolasinac, a free transfer from Schalke, should prove one of the bargains of the 2017-18 campaign.
The problem is that Arsenal's talented players are led by a manager who has long since lost his air of authority. The mastermind behind arguably the greatest side English football has ever seen is now a highly divisive figure among the supporters, many of whom wanted him sacked in the summer - rather than handed a new, two-year contract.
It is unsurprising, then, that this sense of agitation and restlessness has spilled over into the dressing room. Mesut Ozil has yet to extend a contract that expires next summer, while Alexis Sanchez pushed hard to leave the club before the close of the recent transfer window.
Chelsea have their own unhappy players, of course, with Diego Costa remaining a headache for those around Stamford Bridge but the difference to the Sanchez situation is that Conte, unlike Wenger, no longer wants his unsettled striker.
Meanwhile, the one in-demand player he wants to keep above all others, Eden Hazard, has remained utterly unperturbed by the fact that Zinedine Zidane wants him at Real Madrid.
The Belgian winger is happy in west London and remains thoroughly invested in helping Chelsea win major trophies, which is exactly what he did last season, most memorably when he tore Arsenal to shreds in a 3-1 win at the Bridge in February.
Of course, the Gunners gained a modicum of revenge by denying the Blues a domestic double with a surprise win in the FA Cup final but that result, and their penalty shootout success in this season's Community Shield, felt like anomalies, rare success stories in a tale of one-sided rivalry.
In the league, the Gunners have lost each of their last five away trips to west London, with the Blues racking up an aggregate score of 15-2 since January 2013.
Arsenal do, at least, arrive at the Bridge on the back of a morale-boosting win over Koln in the Europa League in midweek but that positivity will quickly vanish if Wenger's men lose to Chelsea. A defeat would also represent the first time that the club has lost their first three away games in the top flight since 1954-55.
Arsenal still have a group of talented players to pick from and, in attack, they compare quite favourably to their London rivals. However, the divide is huge in midfield and defence.
Thibaut Courtois keeps improving and has been a better goalkeeper since well before he ousted Petr Cech from the No.1 shirt at Chelsea in 2014. In front of the Belgian, Chelsea strengthened well during the summer, with Antonio Rudiger adapting well and Andreas Christensen looking like one of the few youngsters who can make the breakthrough at the Bridge.
The gap in quality between the two sides is most obvious in midfield. Chelsea have added over £70 million's worth of talent to complement the skill and industry of Cesc Fabregas and N'Golo Kante, the Premier League's most creative midfielder and the reigning PFA Player of the Season, respectively.
However, the main difference between is Conte. He is arguably good enough to win the title with any group of players from the top six squads in England. His attention to detail and modern tactical approach is the opposite of Wenger's ideology.
Wenger prefers to pick a group of his best players and watch them express themselves but football in 2017 belongs to those with the obsession to immerse themselves in data and video analysis.
Chelsea have enough quality, depth and togetherness to mount a defence of their title. Meanwhile, Arsenal have become the third most likely London club to compete for honours in England.
It's no wonder that Hazard is happy where he is right now, and Sanchez would rather be somewhere else.