United ran out 4-0 winners at Old Trafford to get their Premier League campaign off to a dream start in August, but the fortunes of both sides have varied greatly since then and Chelsea will welcome their opponents to Stamford Bridge as favourites to progress.
It all looked so promising for Manchester United and so bleak for Chelsea after these two sides last met, with United producing an attacking display full of energy, intensity and youthful exuberance to run out 4-0 winners over a Chelsea side coming off the back of a summer transfer window which saw them lose their best player and be denied the chance to replace him by a FIFA ban.
Fast forward two-and-a-half months and the roles have more or less been reversed; Chelsea are the team brimming with exciting young talent whereas United are now eagerly awaiting the next transfer window in order to bolster their squad.
The four-goal drubbing at Old Trafford may have been harsh on Chelsea, but it also acted as a valuable lesson for Frank Lampard on his Premier League managerial debut, and the club legend appears to now be warming to life in the Stamford Bridge dugout.
After winning just two of his opening eight matches in charge, Lampard has now overseen a run of seven successive wins across all competitions which has lifted the Blues into the top four of the Premier League and to the top of their Champions League group.
Win number seven came in some style as Christian Pulisic's perfect hat-trick inspired them to a 4-2 victory at Burnley on Saturday, although the two they conceded late on were another reminder of the biggest area for improvement needed under Lampard.
Only Manchester City and Leicester City have scored more goals in the Premier League this season, but only the bottom three have conceded more too, and Chelsea will know that any chance of silverware this term will require them to fix those holes at the back.
The EFL Cup provides Lampard with his first chance to get an early trophy under his belt, and they certainly made a confident start in their quest to reach a second successive final by hammering Grimsby Town 7-1 in the previous round - a result which kicked off their winning streak.
United will provide sterner opposition than Grimsby, of course, but you have to go back to January 2013 for the last time Chelsea lost an EFL Cup game at home and their recent form will make them all the more confident of redeeming themselves for the last meeting between these two sides.
Lampard may wish that this game had come a week earlier, though, with United beginning to enjoy a change in form during a seven-day spell which saw them become the first team to take points off Liverpool and win back-to-back away games against Partizan Belgrade and Norwich City.
Ole Gunnar Solskjaer's side had not won on the road in any competition since March prior to that, while Sunday's victory over Norwich was their first away from home in the Premier League for exactly eight months.
It was also the first time in 13 matches since the opening-day edition of this fixture that United had managed to score more than one goal in a game, and their three-goal haul could have been greater had Tim Krul not saved two penalties too.
The Red Devils have a torrid record from the spot in recent times and will therefore be hopeful that this match does not go to a shootout - which will be the case if it is all square after 90 minutes.
Victory on Wednesday would see United win three games in a row for the first time since March, although they will be aware that it was Lampard's Derby County side that knocked them out of this competition in the third round last season.
United almost suffered an even bigger shock at the same stage this term as League One Rochdale took them all the way to penalties at Old Trafford before a side including Paul Pogba, Jesse Lingard and Aaron Wan-Bissaka scraped through.
Solskjaer's side will need to be much better if they are to continue their revival at Stamford Bridge as they take on a team who sit seven points ahead of them in the Premier League table.
Chelsea EFL Cup form: W
Chelsea form (all competitions): WWWWWW
Man Utd EFL Cup form: W
Man Utd form (all competitions): DDLDWW
Solskjaer revealed after Sunday's win over Norwich that Pogba is not expected back until December as he continues to struggle with an ankle injury.
The Frenchman is joined on the sidelines by Eric Bailly, Axel Tuanzebe, Timothy Fosu-Mensah and Diogo Dalot, while Nemanja Matic and Luke Shaw are nearing their returns but may not be ready to start this match.
Ross Barkley and Ruben Loftus-Cheek are also on the road to recovery but may not be ready in time to feature in this match, although the latter is an outside possibility to be handed game time off the bench following a lengthy Achilles absence.
Reece James, Olivier Giroud, Callum Hudson-Odoi and Pedro are among the players who will be hopeful of a run-out, while Pulisic will no doubt be keen to keep his spot following his perfect hat-trick at the weekend.
Chelsea possible starting lineup:
Caballero; James, Zouma, Tomori, Alonso; Jorginho, Gilmour; Pedro, Mount, Hudson-Odoi; Giroud
Man Utd possible starting lineup:
Romero; Wan-Bissaka, Maguire, Rojo, Williams; McTominay, Fred; Lingard, Mata, Chong; Greenwood
We say: Chelsea 2-1 Man Utd
Chelsea may be much-changed from the team that suffered that opening-day defeat, but that will not lessen their desire to make amends. The Blues are in fine form at the moment and should have enough to halt United's own revival in its tracks at Stamford Bridge.
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