Dougie Freedman suffered his first defeat as Bolton manager as Michael Chopra grabbed a last-minute winner for Ipswich at the Reebok Stadium.
A 25-yard strike from Mark Davies put Bolton ahead before DJ Campbell scored a penalty, awarded for a Tyrone Mears foul on Daryl Murphy.
Substitute Chopra secured the win after a mistake from goalkeeper Adam Bogdan.
New manager facts
- Dougie Freedman has 10 points from seven games since he took over at Bolton
- Mick McCarthy has 13 points from seven games since he arrived at Ipswich
It was a fourth win in seven games for Ipswich boss Mick McCarthy, moving them five points clear of the drop zone.
Bolton went into the match unbeaten in their first six games under Freedman - a post-war record for a new Wanderers manager.
Despite an impressive display in a 2-1 win at Blackburn during the week, Freedman made three changes to the Bolton starting line-up - recalling Mark Davies following suspension and restoring David Ngog and Marcos Alonso to the starting line-up.
And the changes seemed to have paid off when Davies exchanged passes with Jay Spearing before unleashing a sublime shot that dipped into the top corner.
Despite dominating the first half Bolton were unable to add to their lead.
McCarthy's side grew into the game after the break, drawing level with 20 minutes to play.
Bradley Orr played the ball in to Daryl Murphy who nutmegged Zat Knight before being brought down by Mears.
Bogdan dived the right way but Campbell's spot-kick found the corner.
And it was left for Chopra to score his third goal of the season, with Ipswich recording back to back wins for the first time since March.
Bolton boss Dougie Freedman: "Ipswich thoroughly deserved to win the match and we've got no complaints.
"I felt for 70 minutes we played very well and were the better team because we were creating opportunities. We probably actually did enough to win the match.
"We didn't take those chances though, and in the last 15 minutes we were a bit edgy. That gave them the impetus and the chance to make us pay and they did that to us in the end."
Ipswich boss Mick McCarthy: "I'm delighted with the win and I really wanted to win this game.
"I thought that it was fairly even throughout and in the end that the three substitutes we brought on won it for us.
"It's really cliched but you've just got to take it one game at a time. There is a good spirit here now which wasn't here when I first came.
"There was a lot of finger pointing then but now we all seem to be pushing in the right direction. We're nowhere near to safety just yet though, and we just need to keep looking to pick up maximum points."
Live Text Commentary
Full Time The referee brings the game to a close.90:00 +2:01
Bradley Orr takes a shot. Save by Adam Bogdan. Short corner taken by Lee Martin.89:52
The assist for the goal came from Bradley Orr.89:52 Goal scored
Goal! - Michael Chopra - Bolton 1 - 2 Ipswich Michael Chopra finds the back of the net with a goal from inside the area high into the middle of the goal. Bolton 1-2 Ipswich.88:51
Daryl Murphy takes a shot. Adam Bogdan makes a save. Lee Martin takes a outswinging corner from the right by-line played to the near post, clearance by Tyrone Mears.88:21
Jay Spearing fouled by Lee Martin, the ref awards a free kick. Adam Bogdan takes the free kick.87:23
Free kick awarded for an unfair challenge on Bradley Orr by Jay Spearing. Direct free kick taken by Stephen Henderson.86:37
Effort from the edge of the penalty box by Jacob Butterfield goes wide of the right-hand upright.84:17
Lee Martin takes a shot. Adam Bogdan makes a save.80:21
Free kick awarded for a foul by Benik Afobe on Lee Martin. Stephen Henderson takes the direct free kick.79:40
Jay Emmanuel-Thomas takes a shot. Adam Bogdan makes a save.77:39
Free kick awarded for an unfair challenge on Tyrone Mears by Michael Chopra. Jacob Butterfield takes the free kick.77:39 Booking
Booking Michael Chopra goes into the book for unsporting behaviour.76:48 Substitution
Substitution Keith Andrews leaves the field to be replaced by Jacob Butterfield.75:05 Substitution
Substitution Michael Chopra on for DJ Campbell.73:10
DJ Campbell challenges Marcos Alonso unfairly and gives away a free kick. Samuel Ricketts restarts play with the free kick.71:20 Substitution
Substitution Benik Afobe is brought on as a substitute for Kevin Davies.71:20
Kevin Davies is flagged offside by the assistant referee. Stephen Henderson takes the indirect free kick.69:39 Goal scored
Goal! - DJ Campbell - Bolton 1 - 1 Ipswich Placed penalty scored by DJ Campbell. Bolton 1-1 Ipswich.69:09 Booking
Booking Tyrone Mears receives a yellow card.
Tyrone Mears gives away a Penalty for an unfair challenge on Daryl Murphy.64:05
Unfair challenge on Chung-Yong Lee by Lee Martin results in a free kick. Chung-Yong Lee takes the free kick.62:48 Substitution
Substitution Chung-Yong Lee joins the action as a substitute, replacing Chris Eagles.55:44
Chris Eagles takes the inswinging corner, save made by Stephen Henderson.53:00 Substitution
Substitution Daryl Murphy comes on in place of Tyrone Barnett.53:00 Substitution
Substitution Jay Emmanuel-Thomas replaces Andy Drury.53:00
Lee Martin challenges Kevin Davies unfairly and gives away a free kick. Chris Eagles has a direct shot on goal from the free kick.52:08
Kevin Davies takes a shot. Stephen Henderson makes a comfortable save.49:15
Shot by Kevin Davies. Save by Stephen Henderson.45:01
The referee blows his whistle to start the second half.45:00 +1:22 Half time
Half Time The first half comes to an end.44:48
DJ Campbell is ruled offside. Free kick taken by Adam Bogdan.41:48
Chris Eagles produces a right-footed shot from the edge of the area and misses to the left of the target.38:45
Corner taken by Lee Martin from the right by-line played to the near post, Zat Knight manages to make a clearance.30:03
Jay Spearing concedes a free kick for a foul on DJ Campbell. Strike comes in from Lee Martin from the free kick.29:23
David Ngog is ruled offside. Indirect free kick taken by Stephen Henderson.27:39
Foul by Tyrone Mears on Lee Martin, free kick awarded. Free kick taken by Stephen Henderson.27:03
Guirane N'Daw gives away a free kick for an unfair challenge on Keith Andrews. Free kick taken by Keith Andrews.25:58
Foul by Kevin Davies on Bradley Orr, free kick awarded. Direct free kick taken by Aaron Cresswell.25:15
Effort from 12 yards by Chris Eagles. Save by Stephen Henderson.18:58
Chris Eagles fouled by Guirane N'Daw, the ref awards a free kick. Tyrone Mears takes the direct free kick. Lee Martin takes a outswinging corner from the right by-line played to the near post.17:34
Adam Bogdan restarts play with the free kick. Short corner taken by Chris Eagles from the right by-line.17:34 Booking
Booking DJ Campbell is shown a yellow card.17:28
DJ Campbell challenges Keith Andrews unfairly and gives away a free kick.15:41
Effort from the edge of the penalty box by Kevin Davies goes wide of the right-hand upright.13:44
David Ngog challenges Carlos Edwards unfairly and gives away a free kick. Stephen Henderson restarts play with the free kick.9:54
Foul by David Ngog on Carlos Edwards, free kick awarded. Luke Chambers takes the free kick.9:15
The assistant referee signals for offside against David Ngog. Stephen Henderson restarts play with the free kick.7:24
Marcos Alonso produces a right-footed shot from outside the box and misses left. Chris Eagles takes a outswinging corner.5:04
Assist by Jay Spearing.5:04 Goal scored
Goal! - Mark Davies - Bolton 1 - 0 Ipswich Mark Davies finds the net with a goal from just inside the area to the bottom right corner of the goal. Bolton 1-0 Ipswich.3:33
Lee Martin takes a shot. Tyrone Mears gets a block in. Keith Andrews takes a shot. Corner taken by Chris Eagles from the right by-line.3:06
DJ Campbell concedes a free kick for a foul on Samuel Ricketts. Free kick taken by Adam Bogdan.0:19
Lee Martin is adjudged to have handled the ball. Samuel Ricketts takes the direct free kick.0:00
The match begins.
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