Chelsea left Portman Road empty-handed as Ipswich Town scored in either half to secure a 2-0 win.
The Blues created plenty of chances in either half and Joao Felix even had a goal ruled out for offside with the score at 1-0.
But Liam Delap's penalty after just 12 minutes and Omari Hutchinson's strike early in the second half ensured it was the Tractor Boys who took the victory to move within one point of 17th-place Wolves.
Five changes
Enzo Maresca decided to freshen up his side with the introduction of Filip Jorgensen, Axel Disasi, Noni Madueke, Joao Felix and Christopher Nkunku.
It meant Jorgensen was in goal once more, with a back four of Disasi, Tosin Adarabioyo, Levi Colwill and Marc Cucurella. Moises Caicedo and Enzo Fernandez were in midfield, with Cole Palmer ahead of them, and Madueke and Joao Felix on the flanks. Nkunku led the line.
There was also a return to the matchday squad for the first time since November 10 for Reece James following his injury.
Ipswich made four alterations to the XI, including changing their goalkeeper as Arijanet Muric was replaced by Christian Walton.
It was Ipswich who had the first chance, as a cut-back from former Blue Hutchinson was turned goalwards by Nathan Broadhead but the shot from eight yards out was blocked.
Blues go behind
The hosts then took the lead on 12 minutes from the penalty spot. Leif Davis picked out the run from Delap with a pass from the left flank and the striker just got to the ball before the diving Jorgensen, who was adjudged to have brought him down despite the goalkeeper's complaints.
Delap, who played under Maresca for Manchester City Under-23s, beat Jorgensen from the penalty spot despite the goalkeeper guessing the right way.
It could have been 2-0 a minute later when a blocked clearance bounced into the path of Delap just inside the penalty area and the 21-year-old smashed a first-time effort towards the far top corner which had to be tipped away by Jorgensen.
So close
Chelsea were inches away from equalising twice in a matter of minutes midway through the opening period. First, Palmer's low free-kick from 20 yards hit the inside of the post and bounced out into the six-yard box, where Nkunku dived in to tackle as the ball was about to be cleared and Walton recovered in time to save the rebound.
The Blues did have the ball in the back of the net when Palmer's inswinging cross from the right then picked out the run of Joao Felix at the far post and he smashed into the roof of the net. But after a lengthy VAR check, the on-field decision from the referee and assistant was overturned and offside was given.
Chelsea were increasingly on top as the half progressed and had a number of efforts over the next ten minutes. Cucurella struck a powerful effort wide, Caicedo sent a shot from 18 yards over the bar and Joao Felix forced Walton into another stop.
Ipswich showed their threat on the counter, though, when Delap created enough space to hit a fierce shot which would have nestled inside Jorgensen's near post had the goalkeeper not tipped it wide.
Chelsea continued to search for the equaliser and Fernandez had a goal-bound effort from close to the penalty spot blocked shortly before half-time.
Wonder save
The Blues would have levelled in first-half injury-time had it not been for an outstanding save from Walton. Some slick build-up play involving Fernandez and Joao Felix ended with Palmer curling a 20-yard strike towards goal but the Ipswich keeper made a stunning fingertip stop to keep his team in front heading into the break.
Chelsea started the second period strongly and just two minutes after the restart, Fernandez stood up a cross for Joao Felix and his header had to be cleared off the line.
A minute later, Disasi released Madueke and he had a low drive towards the near post diverted wide by Walton. The resulting corner nearly found its way into the goal but Ipswich's defenders just managed to scramble the ball away.
Ipswich double their lead
But for all of the Blues' early pressure and chances, it was Ipswich who scored the game's next goal. Disasi's misplaced pass was collected by Delap close to the halfway line and after Tosin did well to hold up the striker, he laid the ball back to Hutchinson and the winger sent a low shot into the far bottom corner.
Maresca reacted immediately by bringing on Nicolas Jackson, with Nkunku moving into the left-side number 10 role which Joao Felix had been occupying, as Cucurella continued to offer the width.
Disasi fired over from distance and Palmer almost caught out Walton with a cross-shot before Maresca then introduced Jadon Sancho in place of Nkunku with 20 minutes remaining.
The Blues kept pushing. Palmer had a shot blocked, there was a penalty appeal for handball and Jackson shot wide when one-on-one, although he was offside regardless.
Ipswich were still a threat on the counter though and Delap had a shot from a tight angle tipped over midway through the half.
Pedro Neto and Malo Gusto were also introduced as we entered the final quarter of an hour but Ipswich managed to see out the game to secure all three points.
What it means
The Blues’ defeat to Ipswich means we are still in fourth position, one point behind Arsenal in third and two points below Nottingham Forest in second.
What next
Our next game will be away to Crystal Palace on Saturday 4 January at 3pm GMT. The fixture will not be televised in the UK but you can follow all the action in our match centre, with live commentary and minute-by-minute updates.
The teams
Ipswich Town: Walton; Burns (Johnson 86), O’Shea, Woolfenden, Greaves, Davis; Morsy, Cajuste (Phillips 77); Hutchinson (Al-Hamadi 90+3), Broadhead (Szmodics 77); Delap (Taylor 90+3)
Unused subs: Muric, Townsend, Chaplin, J. Clarke
Bookings: O'Shea 32, Delap 83, Davis 88
Scorers: Delap 12 (p), Hutchinson 53
Chelsea: Jorgensen; Disasi (Gusto 77), Tosin, Colwill, Cucurella; Caicedo, Fernandez (c); Madueke (Neto 77), Palmer, Joao Felix (Jackson 55); Nkunku (Sancho 65)
Unused subs: Sanchez, James, Acheampong, Veiga, Guiu
Bookings: Caicedo 67, Gusto 88, Colwill 88
Referee: John Brooks
Attendance: 29,968