Frank Lampard was taught a harsh lesson back in August, but Wednesday's Carabao Cup fourth-round tie, live on Sky Sports, provides an opportunity to show how far his side has come.
Lampard was in charge of Derby last season when his side knocked Manchester United out of the Carabao Cup at the third-round stage - a 2-2 draw before the Rams won 8-7 on penalties at Old Trafford.
Live Carabao Cup
His last meeting with the five-time League Cup winners was less enjoyable, however.
United were ruthless in a 4-0 win over Chelsea on the opening weekend of the season but Ole Gunnar Solskjaer does not expect a similar scoreline at Stamford Bridge.
Lampard's Chelsea are on a seven-game winning run in all competitions, with youngsters Tammy Abraham, Mason Mount and Fikayo Tomori cementing their first-team positions after spending last season on loan.
"It is a very exciting team," said Solskjaer. "Frank has got players that have been on loan for one or two seasons in the Championship.
"The difference between my youngsters is that they are almost stepping right now onto the scene."
United inflicted a harsh lesson on Lampard in his first Premier League assignment as Chelsea head coach.
Marcus Rashford opened United's account from the penalty spot on 18 minutes, but Chelsea struck the woodwork twice through Tammy Abraham and Emerson Palmieri before the end of a promising first half.
Chelsea had more chances and more possession but a combination of wastefulness in front of goal and defensive errors cost them dearly, as Anthony Martial doubled United's lead and Rashford doubled his tally in the space of two second-half minutes.
Summer signing Daniel James came off the bench to complete the rout for Solskjaer's side, who were guided to a first clean sheet of the season by assured performances from Harry Maguire and Aaron Wan-Bissaka on their Premier League debuts for the club.
How Chelsea recovered
The 4-2 victory over Burnley at Turf Moor was a milestone result for Chelsea. The Blues have won four consecutive top-flight away games while scoring at least three goals in each match for the first time in their history.
Furthermore, Lampard's young side have won their last six away games in all competitions - only once in their history have they won more consecutively on the road (seven between February and April 1989).
Chelsea sit fourth in the Premier League table with 20 points from their opening 10 games - and this has all been achieved without Eden Hazard, who was sold for £130m to Real Madrid last summer.
The Belgian had been the focal point of their play under Maurizio Sarri - and the 4-0 loss to United at Old Trafford indicated that Lampard would be in for a long, hard season without the ability to conduct any business in the transfer market.
But where other teams have struggled to replace the sale of a superstar, Chelsea have risen to the challenge. Mount was unfairly criticised in some quarters following his first Premier League start, but he has been a revelation since.
The 20-year-old has scored four league goals and created more chances (19) than any other Chelsea player - and the Blues now harbour realistic hopes of securing Champions League football next season via their league position.
"We're improving, and that's the main thing in football," said Lampard at Tuesday's press conference. "That's what we've been striving for since the beginning of pre-season.
"The really pleasing thing is that we've seen good signs in those seven wins. There has been lots of things we like and lots of things where we know we can improve.
"I did expect high expectations anyway, because of the nature of Chelsea and managing this club. People do expect - transfer ban or no transfer ban.
"I don't mind it and I'm used to it as a player. It's a positive, and I would rather be managing expectation in this way than flipping it around."
Have United turned a corner?
Sky Sports' Paul Merson:
"It's been a good week for them. They stopped Liverpool, then they went to Partizan and kept a clean sheet and they would have wanted to keep a clean sheet against Norwich.
"They had to beat Norwich surely, they got beaten 5-0 by Aston Villa at home and the last thing you need is to be going there and getting beaten - that would have been a disaster.
"We put such a high bar on Man Utd because they're the biggest club in the world and now we're talking about having a good week drawing at home to Liverpool and beating Partizan and Norwich away. I didn't think in my wildest dreams that I'd be sitting here talking about a good week like that for Man Utd.
"A few years ago, it wouldn't even come up, it would just be run of the mill. Liverpool don't win at Old Trafford and they go and win the other two games - that's what is expected, but this is where they are at the moment.
"All it is with Man Utd is a bit of consistency and confidence. You only have to win three on the trot and before you know it, you're back in the top-four race and that's what they're in.
Ole: Fred to replace Pogba 'for a while'
Ole Gunnar Solskjaer says Fred will replace the injured Paul Pogba in the Manchester United midfield "for a while".
"Anthony Martial is a top player, he's better than a lot of the players they've got. If you're the manager, you're always going to hope a player like him is coming back into the team.
"On his day, he can rip anybody apart and if you get him and Marcus Rashford playing, they're going to hurt teams and fly up the table but it's all about consistency and they've got to put in performances like they did against Liverpool every week."
What the managers have said
Manchester United boss Ole Gunnar Solskajer: "I think Frank has done a good job because the performance against us was good. The result was bad.
"We held our hands up as well and said: '4-0? Yeah, flattering'.
"We were pegged back, they pressed us, but we scored two goals, the second and the third within a minute which decided the game for us, so we didn't think we were 4-0 better than them but it's going to be an interesting game."
"It feels like a million miles away... they can hurt you during moments and they did it to us four times in a game that we performed pretty well in."
Chelsea head coach Frank Lampard said: "I've said nothing about that," when asked if the opening-day loss had been mentioned in the lead up to Wednesday's tie.
"It feels like a million miles away. I'm not disregarding it, and when you play against a top team like Manchester United with top players, they can hurt you during moments and they did it to us four times in a game that we performed pretty well in.
"So I don't think the context of that will be hugely relevant."
Chelsea will once more be without Antonio Rudiger, who is recovering from a groin injury, so Lampard must make a call on whether to start Marc Guehi again after fielding the youngster in the 7-1 win over Grimsby in the previous round.
N'Golo Kante (groin) also remains out and the fixture presents an opportunity for some players who have not been involved heavily recently.
Reece James is likely to start at right-back while goalkeeper Willy Caballero is expected to replace Kepa Arrizabalaga.
Michy Batshuayi, Olivier Giroud, Pedro and Billy Gilmour will all be hoping for another chance to impress.
Manchester United boss Solskjaer hinted in his press conference that James Garner and Brandon Williams could be named in the squad for Wednesday's clash.
"We have not made a decision on who is going to play, but you will probably see the two of them," Solskjaer added.
"Character will be revealed in tough times, but I think they have done excellent, the young kids... I couldn't be any more happy with many of the youngsters."
Solskjaer has used a number of young players this season, particularly in the Carabao Cup and Europa League.
The 19-year-old defender Williams made his debut against Rochdale in the previous round, while fellow teenager Mason Greenwood found the net against the Sky Bet League One club.
- This will be the 185th competitive fixture played between Chelsea and Manchester United, with the clubs facing off in the League Cup for the sixth time.
- Chelsea last faced Man Utd in the League Cup in a fourth-round tie in October 2012, winning a 5-4 thriller in extra-time, with eight different players scoring on that day.
- Chelsea have won 10 of their last 11 League Cup matches at Stamford Bridge, with the only exception being a 0-0 draw with Arsenal in January 2018.
- Man Utd have won six of their last seven League Cup matches against Premier League opposition (L1), including a 3-2 victory in the final against Southampton in 2016-17.
- Man Utd forward Anthony Martial has been directly involved in four goals in his last three starts against Chelsea in all competitions (3 goals, 1 assist).
Follow the Carabao Cup across Sky Sports
On Wednesday, there will be two Carabao Cup games live on Sky Sports. Liverpool host Arsenal - live on Sky Sports Football from 7pm; Kick-off 7.30pm - while Man Utd visit Chelsea - live on Sky Sports Main Event, also from 7pm; Kick-off 8.05pm.
Soccer Special will also be live from 7.30pm on Sky Sports News and Sky Sports Premier League, with live blog coverage across Sky Sports' digital platforms from 6.30pm. There will also be free highlights of each game available after full-time.