Despite putting in a strong performance on the road, second-half strikes from Cole Skuse and David McGoldrick saw Bolton Wanderers taste defeat at Portman Road.
On another day Wanderers would have earned a point in East Anglia as they showed attacking intent and a dogged resolve throughout the contest, but were unable to make their positive presence count.
Skuse's deflected drive not long after the restart gave the hosts the advantage before McGoldrick rounded the victory off moments from full-time with a powerful shot past Ben Alnwick.
Wanderers made two changes from the side that lost at home to Sheffield United with Craig Noone and Filipe Morais coming in for Will Buckley and Adam Armstrong.
There was a change in formation also with manager Phil Parkinson reverting to three at the back. Mark Beevers, David Wheater and Reece Burke playing in defence.
The hosts won the first corner of the game after nine minutes after a swift counter saw Burke thwart the rampaging run of Jordan Spence down the far left channel. The effort came to nothing though.
Wanderers responded through Noone whose probing run and shot was blocked at the expense of a free-kick after Morais was fouled.
Noone tried his luck from range after Josh Cullen laid the ball through to him but the wideman’s effort never troubled Bartosz Bialkowski in the Town goal.
Grant Ward sized up a shot from 25 yards as Ipswich looked to seize the initiative but saw his effort go hopelessly wide of Ben Alnwick’s right hand stick.
Noone, whose hunger to get off the mark in a Wanderers shirt was apparent from the off, had another effort but his strike looped into the grateful arms of Bialkowski.
The winger earned his team a corner moments later when his right-footed effort deflected out of play.
It was a bright, positive start from the visitors who were certainly looking to take the game to the hosts.
Morais was the beneficiary of a sublime pass from Noone after the former Cardiff City man weaved his way into the box, but the Portuguese-born star couldn’t keep his effort on target as Wanderers spurned another chance to break the deadlock.
The next chance fell to Gary Madine whose effort from 30 yards appeared destined for the top left hand corner but for the hands of Bialkowski who palmed away the effort.
There was no question that Wanderers were the better team inside the opening half an hour and should have been at least one goal to the good for all the attacking intent they showed.
Against the run of play, the hosts took the lead moments after the restart after Cole Skuse’s shot from distance took a wicked deflection to flat foot Alnwick. The chance was created courtesy of a great run and cut-back from David McGoldrick on the right hand side.
Wanderers almost responded instantly when Karacan’s drive bounced awkwardly in front of Bialkowski who palmed the effort away.
Wanderers kept their heads held high despite the setback and continued with their attacking endeavour with Madine causing a nuisance to the Town backline.
And frontman would have snatched an equaliser had Wheater not got in the way of him following a goalmouth melee and some intricate attacking play inside the Town box.
At this stage luck wasn’t with the visitors despite their good play throughout the contest.
Alnwick was then pressed into making a crucial save from McGoldrick to prevent Ipswich from going two goal up after Wanderers failed to clear their lines on two occasions.
Parkinson made his first change of the match on 70 minutes with Adam Armstrong coming of for Mark Little.
Madine had another good chance at the far post after he connected to Robinson’s deep cross but couldn’t head the ball on target.
With 13 minutes to go, Parkinson made a double attacking substitution with Aaron Wilbraham and Adam Le Fondre coming on for Madine and Morais.
Any hopes of Wanderers getting back into the contest were dashed minutes from full-time thanks to McGoldrick’s effort.
Despite their strong performance, arguably the best of the campaign, Wanderers weren’t able to get on the scoresheet and succumbed to a cruel defeat.