Both sides have underachieved in the league this season, sitting eighth and ninth respectively in the Premier League table, but they will already have one eye on a top-four challenge next year.
When Jurgen Klopp reflects on his first season in charge of Liverpool, he is likely to have mixed emotions.
There have been a number of highs since the German succeeded Brendan Rodgers in October, with notable wins over Manchester City, Borussia Dortmund and Villarreal, but consistency has been an issue.
The biggest high of the season could be still to come with the Reds having a Europa League final against Sevilla to look forward to a week after welcoming Chelsea to Anfield, as Klopp looks to lead the club to their first European trophy since 2005.
His immediate focus must be on the league, though, and a record of 13 wins, seven draws and eight defeats since Klopp took over has left Liverpool lying in a disappointing eighth place going into the final two games of the season.
Should they fail to improve on that position and also lose in the Europa League final then the Reds would miss out on Europe next season, but they could still finish as high as fifth should results go their way over the next few days.
Sixth place is a more realistic goal and would guarantee them at least the Europa League again next season, although their main focus will be on qualifying for the Champions League with victory over Sevilla in Basel.
Despite having made numerous changes on a weekly basis over the past month, Liverpool have only lost one of their last seven Premier League outings, and another victory on Wednesday could see them climb up to sixth in the standings.
Their most recent outing saw them back up their midweek heroics with a 2-0 victory over Watford on Sunday as the in-form Roberto Firmino got himself amongst the scorers again to extend his record of having contributed to more goals than any other Liverpool player this season.
The Brazilian has been a large part of Liverpool's run of scoring in their last 12 Premier League outings - their longest such streak in the competition since their title near-miss in 2013-14.
Many of Liverpool's better performances in the early days under Klopp came away from home, but they go into Wednesday's match unbeaten in their last 12 games at Anfield in all competitions and having scored 19 goals in their last six.
The crowd have formed a special bond with Klopp since his arrival, and the manager will be eager to give them something to shout about in their final home match of the campaign, even if he has one eye on Basel.
Recent form: WWWDLW
Recent form (all competitions): WDLLWW
It is earlier than planned, but Chelsea's post-John Terry era looks like getting underway at Anfield on Wednesday after the skipper's sending-off last time out.
The 35-year-old earned himself a needless second yellow card deep into stoppage time of his side's dramatic 3-2 defeat at the hands of Sunderland on Saturday, seemingly bringing a premature curtain down on his 21-year association with the club.
It was his second dismissal of the season, which means that he will be banned for the final two matches of the campaign, and with no new contract for the Chelsea stalwart in the pipeline, his stellar career with the club now looks to be over.
It is not a fitting way to finish for a player who has made more than 700 appearances for the club and led them to four league titles, eight domestic cups, the Champions League and the Europa League, and reports have suggested that fans are planning a 26th-minute walkout of the final two games in protest against the club not offering him a new deal, before returning in time for the second half.
It is looking increasingly like his future will be away from Stamford Bridge, though, and just as his final game was a disappointment, so has been the final season of his Chelsea career.
The Blues are now guaranteed to go down in Premier League history as the worst defending champions ever, with their current position of ninth being the highest that they can finish even if they beat Liverpool and their successors Leicester City in their last two games of the campaign.
Chelsea have also conceded 50+ goals in a league season for the first time since 1996-97, and four more in those final two games would see them equal their club-record worst tally of 55 in the Premier League era.
The Dutchman certainly steadied the ship at Stamford Bridge, going unbeaten in the first 15 league games of his second stint as interim boss, but he has since lost three and won just one of his last five games.
Indeed, Chelsea have won just two of their last 10 outings in all competitions, although away from home they have lost only twice in the league since Hiddink took over and have won six of their last nine outings on their travels.
They actually boast a better away record this season than they do at home, despite winning just one of their first nine games on the road.
Recent form: WLLWDL
Klopp has made numerous changes to his side in recent weeks, and that could be the theme again with the Europa League final on the horizon.
Christian Benteke was handed a rare start against Watford as Daniel Sturridge watched on as an unused sub, and that may be the case on Wednesday too should Klopp look to protect his most important players.
Philippe Coutinho, who did start on Sunday, may be given a rest for this game, but Joe Allen earned glowing praise for his goalscoring performance against the Hornets and could get another chance to prove himself.
Divock Origi and Jordan Henderson are in with an outside chance of returning in time for next week's final, but they will play no part in this game, joining the suspended Mamadou Sakho and injured Danny Ings, Joe Gomez and Danny Ward on the sidelines.
Chelsea, meanwhile, will be without the suspended Terry as already mentioned, which could see Matt Miazga handed a start in central defence should Hiddink opt to use the final two games to field some youngsters.
Diego Costa is expected to lead the line once again, though, having been directly involved in 14 goals in his last 14 Premier League games for Chelsea (nine goals, five assists).
Liverpool possible starting lineup:
Mignolet; Flanagan, Skrtel, Toure, Randall; Allen, Stewart, Ojo, Firmino, Ibe; Benteke
Chelsea possible starting lineup:
Courtois; Ivanovic, Cahill, Miazga, Azpilicueta; Mikel, Matic, Willian, Fabregas, Hazard; Costa
Head To Head
Liverpool had gone eight matches without a win in all competitions against Chelsea until the two sides met at Stamford Bridge earlier this season.
Liverpool have not beaten Chelsea at Anfield since a 4-1 win in May 2012, though, while between them these two sides have kept only one clean sheet in the last nine Premier League meetings.
We say: Liverpool 2-1 Chelsea
This match could have a distinct end-of-season feel to it, with Liverpool's main focus being on the Europa League final and Chelsea having little left to fight for. However, the hosts will still want to finish as high as possible in the league and sign off from Anfield in winning fashion, which we think will give them the edge against a Chelsea side in poor form.