Frank Lampard got one over Jose Mourinho as Derby knocked Manchester United out of the Carabao Cup, winning 8-7 on penalties following a dramatic 2-2 draw on Tuesday.
Juan Mata's early strike (2) seemed to put United in control but Derby always carried a threat and on-loan Liverpool man Harry Wilson scored a sensational free-kick from 30 yards (59) to pull the visitors level.
Sergio Romero was then sent off for handling outside the area (68) and Jack Marriott (85) looked like he had won it for Derby after his close-range header was awarded with the help of VAR.
However, Marouane Fellaini forced home a dramatic late header to send the tie to penalties.
There were 15 perfect penalties until Phil Jones was denied by Scott Carson as Derby reached the last 16.
It was a pulsating opening 15 minutes with Derby pushing men forward to test United's defence - but it was the hosts that struck first.
Man Utd: Romero (5), Dalot (6), Bailly (6), Jones (6), Young (5), Herrera (6), Matic (6), Lingard (6), Mata (7), Martial (7), Lukaku (5)
Subs: Fellaini (7), Fred (5), Grant (6)
Derby: Carson (6), Bogle (6), Forsyth (7), Bryson (7), Keogh (6), Tomori (6), Wilson (9), Johnson (7), Mount (8), Bennett (7), Nugent (7)
Subs: Marriott (7), Jozefzoon (7), Wisdom (6)
Man of the match: Harry Wilson
Anthony Martial dazzled at times on the left and he set up the move that was finished by Mata courtesy of a fine left-footed finish.
The goal did not knock Derby's confidence and Mason Bennett was denied by a brave Romero block before Romelu Lukaku and Mata both wasted glorious one-on-one opportunities.
Jose Mourinho made nine changes from the 1-1 draw with Wolves as only Romelu Lukaku and Jesse Lingard kept their place. Anthony Martial was handed a start but Paul Pogba was not in the squad.
Old Trafford has seen some spectacular free-kicks down the years courtesy of David Beckham and Cristiano Ronaldo but Wilson produced one that was on a par with 58 minutes gone. From 30 yards, the Wales international hit a left-footed strike that moved one way then the other, which left Romero stranded and the ball swerved mesmerizingly into the top corner.
There was little response from United, who struggled to get into Martial or Lukaku into game and it was Derby that created the next big moment. Wilson broke the offside trap and Romero could only stop his charge by handling the ball outside the area - a red card followed.
It handed a United debut to former Derby favourite Lee Grant off the bench and he was quick into the action to deny Florian Jozefzoon with a smart save.
Grant could not stop Marriott minutes later when he was on hand to head home the rebound after the impressive Mason Mount's effort had been palmed away by the goalkeeper.
United looked down and out, until one last ball into the box caused panic in the Derby backline and Fellaini forced home the equaliser.
It sent the game to penalties but there was no nerves on show as both teams scored the first 15 attempts. The perfect record was broken by Jones, whose soft attempt was easily pushed away by Carson to send the Rams marching on.
- Wilson is the first player to score a direct free-kick against Manchester United in the League Cup at Old Trafford since Giles Barnes back in January 2009, also for Derby County.
- Romero is the first Manchester United player to receive a straight red card at Old Trafford in any competition since Eric Bailly did so back in May 2017 against Celta Vigo in the Europa League.
- Manchester United have lost each of their last five penalty shoot-outs in all competitions (3x League Cup, 1x FA Cup, 1x Community Shield)
Man of the match: Harry Wilson
A Liverpool youngster shining on the Old Trafford stage will have hurt the locals - and it may not be the last they hear of the left-footed winger. He was outstanding. Always carrying a direct threat with the ball, the 21-year-old looked like a player made for this stage - as shown by his quite ridiculously special free-kick that will live long in the memory. Along with Mount, Lampard looks to have two special talents to work with this season.
United are back in action on Saturday lunchtime against West Ham United while Derby play Bolton in the Sky Bet Championship.