Liverpool manager Jurgen Klopp will endeavour to achieve a managerial first when the Reds head to Goodison Park to face Merseyside rivals Everton on Wednesday night.
The midweek encounter will represent Klopp's final Merseyside derby as Liverpool manager, as the German confirmed in January that he would step down from his job at the end of the season.
Depending on Arsenal's result against Chelsea on Tuesday night, the second-placed Reds could be three points behind the league-leading Gunners by the time they take to the field 24 hours later.
Reigning champions Manchester City are also hot on Liverpool's heels, sitting just one point worse off with a game in hand, but the Reds prevailed 2-0 in their most recent Merseyside derby with Everton in October.
That triumph represented Klopp's ninth from 16 Merseyside derbies in the Premier League, and he could now become the first Liverpool coach to oversee 10 victories against the Reds' bitter adversaries in the competition.
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Klopp out to emulate Sir Kenny Dalglish Merseyside derby record
Liverpool have only been beaten once by Everton in all tournaments since Klopp took charge in October 2015, and his first Merseyside derby towards the end of the 15-16 season ended in a 4-0 Anfield success.
As a result, the former Borussia Dortmund manager could also emulate Sir Kenny Dalglish as just the second Liverpool boss to win both their first and last Merseyside derbies in the league.
Dalglish's maiden and final victories in this matchup came 27 years apart, as he masterminded a 3-2 success in September 1985 during the days of the First Division, before a Steven Gerrard hat-trick saw the Reds triumph 3-0 in 2012.
It is not just managerial landmarks that could be hit in the 244th Merseyside derby either, as Liverpool are just one victory away from registering 100 wins against the Toffees, and they need just three goals to chalk up 150 away to Everton in league action.
Recent history is certainly on the visitors' side too, as Everton are on a 12-game winless Premier League sequence against Liverpool at Goodison Park, their longest streak without a home success against a particular team.
Liverpool dealt major injury blow ahead of Goodison trip
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The Toffees did manage to prevail at Anfield behind closed doors in 2021, but they have since lost four and drawn one of their last five meetings with the Reds, failing to score in each of their last four.
However, Liverpool's hopes of a clinical attacking display have been partially dashed by news of a new injury to Diogo Jota, who picked up a hip issue during the weekend's 3-1 victory over Fulham.
The Portugal international started and scored in that success at Craven Cottage, and he has averaged a goal every 115 minutes in the Premier League, the best of all players with at least five non-penalty strikes.
Klopp revealed in his pre-game press conference that Jota would spend two weeks on the treatment table with the problem, though, joining Ben Doak, Thiago Alcantara, Conor Bradley and Joel Matip on the sidelines.
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