Michael Chopra came off the bench to snatch a last-minute winner for Ipswich and hand Dougie Freedman his first defeat as Bolton manager as it ended 2-1.
Wanderers raced into an early lead courtesy of superb 25-yard strike by Mark Davies.
Bolton proceeded to dominate the opening exchanges but could not add to their advantage, while Lee Martin came closest to finding an Ipswich equaliser before the break.
Despite a pair of early second-half chances for Kevin Davies, Town were growing into the game and DJ Campbell levelled from the penalty spot when Tyrone Mears brought down Darryl Murphy.
That left Chopra to capitalise on some slack handling from Bolton goalkeeper Adam Bogdan and move Ipswich five points clear of the relegation zone following back-to-back wins.
Bolton headed into the match unbeaten in their first six games under Freedman - a post-war record for a new Wanderers manager.
Despite their impressive display against Blackburn at Ewood Park in midweek - where it ended 2-1 - Freedman shuffled his pack again, recalling Mark Davies following suspension and restoring David Ngog and Marcos Alonso to the starting line-up.
Mick McCarthy made one change to the Ipswich side that beat Nottingham Forest 3-1 in midweek, with Andy Drury replacing the injured Luke Hyam.
Town goalkeeper Stephen Henderson touched a Keith Andrews drive over as Bolton served early notice of their intentions, and they were ahead by the sixth minute.
Mark Davies exchanged passes with Jay Spearing before unleashing a sublime shot that dipped into the top corner, leaving Henderson with no chance.
Alonso had an effort from distance deflected behind before Kevin Davies prodded wide as he stretched to meet a pull back from strike partner Ngog, but Ipswich managed to see out the early storm without suffering any further damage.
After the half-hour Martin was the beneficiary of a cleverly worked Town free-kick and saw his strike beaten away by Bogdan.
Wanderers might have extended their lead on the stroke of half-time but Chris Eagles elected to shoot with Kevin Davies well placed.
Henderson produced a magnificent stop when Kevin Davies fired a volley goalwards from Mark Davies' cross in the 50th minute. The veteran striker was thwarted again a few moments later with a header from Andrews' lofted ball.
Despite those opportunities, Bolton were unable to reproduce their earlier fluency and Ipswich drew level with 20 minutes to play.
Bradley Orr played the ball in to Murphy who cutely nutmegged Zat Knight before being brought down by Mears.
Bogdan guessed correctly but Campbell's spot kick nestled in the corner.
Ipswich now appeared the most likely winners and Bogdan saved well with his feet from Martin following good work from Jay Emmanuel-Thomas, who was introduced in place of Andy Drury 10 minutes into the second half.
Bolton substitute Jacob Butterfield cut in from the left to thrash narrowly wide but there would be late heartbreak for the hosts after Knight blocked Murphy's goalbound effort.
The resulting corner, taken by Martin, was half cleared and and when Bogdan failed to hold Orr's well-struck volley, Chopra was on hand to finish.