Despite pleas to keep calm and carry on as normal, the boss got an emotional reception for Sunday's 5-2 FA Cup win over Norwich at the weekend, which kicked off a 'last dance' style run-in for Klopp's Liverpool.
The 56-year-old could still bow out with a perfect sign-off in the form of an unprecedented quadruple. However, the Reds will need to be near flawless for the next four months to have any chance of making that dream a reality — not least in the Premier League.
Liverpool are currently five points clear at the top, but Manchester City have a game in hand and typically like to turn on the afterburners in the second half of the season.
That makes practically every one of the Reds' remaining 17 games feel like a must-win, starting with Chelsea.
The Blues have been ropey this season but are finding form of late and have won seven of their last ten in all competitions.
With some big names returning to fitness, here's how Liverpool could line up for Wednesday's clash.
Goalkeeper & Defence
Having made his comeback off the bench in the win over Norwich, Trent Alexander-Arnold is primed to resume his duties at right back for Liverpool in this one — despite an impressive brace of assists from his deputy Conor Bradley in the FA Cup.
Klopp finally has options at his disposal with Andy Robertson fit again.
Will the 29-year-old be used from the start against Chelsea? It seems more likely that Joe Gomez — one of the surprise stars of the 2023/24 season — will reprise his role, with Robertson more likely to be used back into action over the coming weeks.
Barring a late injury, Alisson is a dead cert to line up behind the back four.
Alexis Mac Allister was left out of Sunday's win as a pre-caution, but should be fit for Wednesday night.
The World Cup winner remains the best option for the deep-lying role, with Wataru Endo's Japan still going strong in the Asian Cup and due to play Bahrain in the last 16 the same night Liverpool take on Chelsea.
Either side of Mac Allister could be Dominik Szoboszlai and Curtis Jones, who have both established themselves as Klopp's preferred engine room operators when available.
Szoboszlai marked his return from injury with an assist, while Jones bagged the opener against Norwich with a header.
James McConnell, who also grabbed an assist in the victory, could well get another bench slot as he chases his a second Premier League appearance.
Darwin Nuñez has made himself undroppable in 2024, with six goal involvement in six outings since the turn of the year.
The Uruguayan is likely to line up alongside the other man who has made Mohamed Salah's absence relatively imperceptible: Diogo Jota.
The Portuguese has an identical goal involvement record to Nuñez this month and is looking as lethal as ever since his return from injury in December.
Whether Jota starts on the left or right is up for debate, with Luis Diaz impressing on both flanks in recent outings. The former Porto man has his smile back according to Klopp and has history against Chelsea, having scored against the Blues at Stamford Bridge on the opening day of the Premier League campaign.
He was also Man of the Match when Liverpool beat Chelsea to win the FA Cup back in 2022.
Predicted starting XI to face Chelsea:
(4-3-3): Alisson; Alexander-Arnold, Konate, Van Dijk, Gomez; Szoboszlai, Mac Allister, Jones; Jota, Nuñez, Diaz