In the 2006-07 League Cup, Liverpool were defeated 6-3
Year in year out, Liverpool and Arsenal's hopes of a title challenge flicker.
But more often than not, those hopes are extinguished quite quickly. The 2016-17 season has been no different and aside from a battle to stay in the lucrative Top Four, both clubs have little to play for in their head to head at Anfield on Saturday evening.
They met on the opening weekend in a seven goal thriller which went Liverpool's way by a 4-3 scoreline.
There have been a few classics between the sides. But one slightly forgotten one dates back to January 2007 in the League Cup quarter finals when Arsenal youngsters saw off Liverpool 6-3 at Anfield - the first time Liverpool had conceded six at home for 77 years. The Reds' starting team included Steven Gerrard, Sami Hyppia, a past-his-peak Robbie Fowler, Craig Bellamy and Jerzy Dudek.
Over the next decade, the promising wave of talent that Arsene Wenger was honing never really came to fruition for one reason or another. But in the mid-2000s, hopes were high that the Frenchman was building a next great generation.
So what became of the starting XI from that 6-3 victory?
Until the signing of Petr Cech in 2015, Wenger had long been accused of not solving the goalkeeping void at Arsenal after the David Seaman-Jens Lehmann era.
Manuel Almunia was one of those goalkeepers in the interim period and he was eventually released in 2012 after some inconsistent performances in previous campaigns.
He retired in 2014 aged 37 after two years at Watford due to medical advise regarding a heart condition.
Most recently the Spaniard has worked as a coach in the United Arab Emirates with club side Al Jazira.
Never a regular for the first team after coming through the youth ranks, the right back moved onto Middlesbrough and then Millwall. In 2016 he was released from his most recent club Dagenham & Redbridge.
But now he could end up in the League of Ireland as he has been on trial at Bray Wanderers as confirmed by manager Harry Kenny.
A one-time Invincible, the centre back went on to win the Premier League and FA Cup with Manchester City before joining Liverpool. The Ivorian is now at Celtic with former Reds manager Brendan Rodgers.
The Swiss international defender left Arsenal in 2014. But by then he had already had a couple of loan spells in the German Bundesliga, where he finds himself now with a struggling SV Hamburg.
Arsenal's Julio Baptista celebrates his goal. Picture by Mike Egerton EMPICS Sport
Like Djourou, much of his final years at Arsenal were spent out on loan before he finally departed permanently for QPR in 2011. He would spent five years at Loftus Road before joining Nottingham Forest in the Championship last summer.
The Arsenal winger is the only player from the team on January 9th 2007 who is still part of the squad. While he has had a reasonably decent career at the Emirates and is a regular, he has never matched the potential expected of him despite a strong start to this season. Injuries have also been unhelpful to his development.
No longer loved by Arsenal fans. The World Cup winning former captain burned his bridges with some supporters by signing for London rivals Chelsea after he returned from a short-lived homecoming at Barcelona.
He scored against Arsenal in the recent 3-1 result between the sides with a lobbed finish after a poor kick out by Petr Cech.
The ex-Cameroon international and nephew of former Liverpool defender Rigobert Song did develop into a first team player for Arsenal briefly.
But a move to Barcelona in 2012 did not work out and although he had a slight renaissance on loan at West Ham in 2014-15, the 29 year old now finds himself in Russia with Rubin Kazan.
He scored Arsenal's third goal just before half time in the 6-3 victory over Liverpool.
The Brazilian midfielder was also expected to develop after getting regular game time as an emerging player at Arsenal.
But after spending 2011 to 2013 on loan at Sao Paulo, he left for the same club permanently and joined Al Wahda in the UAE in 2015, although he had a short-lived loan back to Brazil with Cruzeiro.
Arsenal's Cesar Julio Baptista celebrates his second goal with Theo Walcott.
Picture by Mike Egerton EMPICS Sport
The star of the night in the 6-3 win, the Brazilian scored four goals on the night against Liverpool.
The former Sevilla star had only been on loan at Arsenal from Real Madrid and saved his best form for the League Cup where he would six goals in three matches.
Now 35, he spent the 2016 MLS season alongside ex-Brazil team-mate Kaka at Orlando City. The franchise did not offer him a new contract however.
The French striker has had a nomadic career between loan deals and permanent transfers. Football has taken the 33 year old back to France where he is on the books at Lorient. He scored Arsenal's opening goal against Liverpool.