David McGoldrick's second half penalty kick ensured that Wanderers left Suffolk empty handed as they were defeated 1-0 by Ipswich Town.
The striker, who won the spot-kick himself, calmly slotted the ball past Andrew Lonergan in the 55th minute, with the Whites unable to find a response on a bitterly cold Saturday afternoon at Portman Road.
Wanderers’ starting line-up against the Tractor Boys saw just one change to the side which turned out against Queens Park Rangers on Tuesday evening, with Lukas Jutkiewicz handed his first start for the club following Craig Davies’ loan move to Preston on Friday afternoon.
Meanwhile, Liam Trotter, a deadline day acquisition from Millwall, took his place amongst the Bolton substitutes.
Wanderers started brightly, with Jutkiewicz forcing the hosts under pressure early on after connecting with a hopeful punt downfield from deep in the Bolton defence, but the ball was smuggled away for a corner.
Mick McCarthy’s side soon gave the Whites a glimpse of their own danger in front of goal however, with leading goal scorer David McGoldrick unable to keep his effort down from close range in the fourth minute of the game.
Moments later though Jutkiewicz was back in the thick of the action with his looping header from a matter of yards out sailing narrowly past the upright, before playing the ball into the feet of Darren Pratley who had broken free of the Ipswich defence, only to be deemed narrowly offside.
An impressive start from the Whites, they seemed destined to break the deadlock with 11 minutes on the clock as following a scintillating run from Tim Ream down the left flank, neither Jutkiewicz nor Mark Davies could capitalise on some dubious Ipswich defending in the area.
Having struggled to force their way into Wanderers territory in the opening stages, Frank Nouble almost stunned the visitors with an effort from a narrow angle, but Matt Mills got enough on the shot to deflect it past Andrew Lonergan’s far post.
The chance seemed to be just the tonic which Ipswich needed, with the Bolton keeper being forced into a superb save to deny Aaron Cresswell what would have been an incredible strike from all of 30 yards from the resulting corner.
An incident involving a head injury to Cole Skuse halted play just short of the half hour mark, with the Ipswich man leaving the field with the help from the club’s medical staff and being replaced by Anthony Wordsworth.
The stoppage appeared to knock the home side out of their stride, with Dean Gerken being forced into a smart save from close range to deny an unmarked Neil Danns the opening goal of the clash shortly after following a great pass from Jay Spearing.
As the clock ran down, it was undoubtedly Wanderers who were in the ascendancy with Jutkiewicz proving himself a nuisance once again as Christophe Berra almost headed into his own net under pressure from the frontman, while Pratley attempted an ambitious acrobatic effort which failed to trouble Gerken.
Having looked dangerous through the first period, Jutkiewicz looked to have snatched the lead for the Whites on the stroke of half time as he turned his man on the edge of the area, but the loanee scuffed his shot so it trickled agonisingly past the post.
After finishing the first half on a high, Wanderers almost broke the deadlock moments after the restart as Alex Baptiste found himself unmarked in the box and unleashed from a narrow angle, but Gerken was equal to his effort to keep the scores level.
With the full backing of a vocal Portman Road faithful however, the home side enjoyed a spell of pressure soon after with Stephen Hunt and Nouble testing the Bolton defence.
Their determination was to pay off however in the 55th minute as following chaos in the penalty area, Lonergan was adjudged to have fouled McGoldrick in the area, with the striker slotting the resulting spot-kick past the Bolton keeper.
Undoubtedly cruel on Wanderers following their showing thus far in the game, Dougie Freedman threw Chris Eagles into the mix in place of Pratley to provide some added fire power in a bid to drag the Whites back into the clash.
Ipswich were clearly brimming with confidence however, with Hunt’s swinging effort from the edge of the box forcing Lonergan into another good save on the hour mark while Jay Tabb’s long range shot was deflected away with a goal seeming imminent.
The Whites were clearly stunned by the home side’s opener, with Freedman’s side struggling to break out of their own half as Ipswich lay siege on the Bolton goal with Daryl Murphy coming close to doubling the Tractor Boys’ tally following good work from McGoldrick.
The Ipswich frontman looked set to extend his side’s lead with 12 minutes remaining as he powered through midfield and to the edge of the area, but his effort was blocked by the body of Tim Ream, much to the relief of the travelling Bolton faithful.
Having entered the fray earlier in the half, Eagles offered some hope of Wanderers rescuing a result from the game with a well taken curled effort, but Gerken comfortably scooped the ball to safety to the frustration of the winger and his teammates.
With three minutes of stoppage time indicated, Bolton enjoyed one last opportunity as Spearing played the ball into a bustling penalty area, but Ipswich cleared their lines to ensure that all three points remained theirs.