Late goals from Enes Unal and Dango Ouattara saw Bournemouth come from behind to condemn Ipswich to a crushing 2-1 defeat.
Town blew another Portman Road lead as their wait for a first Premier League home win continued following some drama at the death.
Conor Chaplin’s first Premier League goal looked to have finally ended Town’s duck in front of their own fans.
But for the fourth time this season they were pegged back at home after taking the lead as Unal equalised for the Cherries three minutes from the end.
Fellow substitute Ouattara then grabbed a winner deep into stoppage time for the Cherries, who earlier in the season had scored three times from the 87th minute on to beat Everton 3-2. Sunday’s win made it three successive victories for Andoni Iraola’s side.
Bournemouth would have taken the lead after only 10 minutes had Marcus Tavernier not missed an open goal from two yards out. Milos Kerkez drilled a low ball across the face of goal but Tavernier somehow put the ball wide at the far post.
But Ipswich quickly took control and Liam Delap hooked a shot wide, Cameron Burgess headed just over and Omari Hutchinson’s volley was just too high.
The goal arrived in the 21st minute with Bournemouth struggling to clear a Leif Davis throw-in from their penalty box. Burgess neatly played the ball back for Chaplin to rifle across Kepa Arrizabalaga and into the net from 15 yards out.
Since joining Town three years ago in League One, Chaplin had scored 48 goals to help them to back-to-back promotions and he gleefully celebrated his first in the top flight.
In a frantic end to the first half Ipswich had a goal disallowed from a corner for a shove by Delap, before Tavernier pinged a shot against the foot of the far post.
Kluivert had taken a tumble under a challenge from Burgess in the area moments earlier, and Cherries boss Iraola was booked for arguing against the decision not to give a penalty.
Burgess then made a goal-saving challenge to bail out his captain Sam Morsy, who lost possession on the halfway line to let Kluivert through on goal.
Ipswich had led in previous home matches against Fulham, Leicester and Aston Villa this season and drawn all three.
Bournemouth could sense the tension and almost equalised when Unal headed Dean Huijsen’s cross just over the top.
The second goal which would have calmed Ipswich nerves almost came with 20 minutes left when Sam Szmodics’ shot was saved by Kepa with the rebound just eluding Delap.
Instead, with time running out, Ouattara’s cross eluded keeper Arijanet Muric and Unal bundled the ball in at the far post with Burgess unable to clear from under the crossbar.
And the comeback was complete five minutes into stoppage time when David Brooks’ shot was saved by Muric and Ouattara buried the rebound.
Ipswich announced after the match that “a medical emergency” occurred in the directors’ box during the second half, later confirming that club ambassador and former player Simon Milton had been taken ill but was “stable and communicating”.