The Swans bowed out of the FA Cup in the fourth round after going down to defeat to Premier League rivals Bolton at the Reebok Stadium.
Luke Moore had put the Swans ahead in the 44th minute with a fine solo goal but ex-Swan Darren Pratley levelled just a minute later with a neat header.
Bolton grabbed the winner through Chris Eagles, who tapped home from close range after Gerhard Tremmel had parried Martin Petrov's shot in the second half.
The Swans made ten changes with Ashley Williams the only survivor from the side that lost at Sunderland.
Josh McEachran made his first start for the club in a midfield that also saw Kemy Agustien and Mark Gower return to the fold.
Gerhard Tremmel made his second start in the competition between the sticks while Fede Bessone was included in the starting XI for the first time since his return to the club.
With Steven Caulker unavailable due to parent club Spurs not wanting him cup tied, Garry Monk went back into the fold to lead the side alongside Ashley Williams while Jazz Richards got the nod at right-back.
Out wide, Luke Moore and Wayne Routledge supported Leroy Lita in a new-look attack.
There was a strong bench, with the most notable marking the return of Alan Tate from a broken leg.
For the hosts, ex-Swans Sam Ricketts and Darren Pratley went against their former clubs as Owen Coyle made three changes to his starting XI.
Bolton: Adam Bogdan, Chris Eagles (Tuncay, 90), Martin Petrov, Mark Davies, Sam Ricketts, Nigel Reo-Coker (capt), Darren Pratley (Fabrice Muamba, 79), David Ngog (Kevin Davies, 74), Dedryck Boyata, David Wheater, Joe Riley.
Subs: Jussi Jaaskelainen, Paul Robinson, Michael O'Halloran, Tyrone Mears.
Swans: Gerhard Tremmel, Jazz Richards, Garry Monk (capt), Ashley Williams, Fede Bessone, Mark Gower (Joe Allen, 79), Kemy Agustien, Josh McEachran, Wayne Routledge (Nathan Dyer, 66), Luke Moore, Leroy Lita (Danny Graham, 66).
Subs: Jose Moreira, Alan Tate, Angel Rangel, Gylfi Sigurdsson.
It was the hosts who made the brighter start, with Sam Ricketts seeing his header forcing Gerhard Tremmel into conceding a corner following Chris Eagles's free-kick into the penalty area after seven minutes.
Tremmel was again called into action coming up to the halfway point of the half as David Ngog raced clear of the Swans defence and headed towards goal. But the German keeper was up to the task, sliding out to block Ngog's shot out for a corner via his foot.
The hosts kept the pressure on, and after a number of corners, Mark Davies drilled a low shot towards the bottom corner but Tremmel dived along goal to keep it out.
Eagles then fired high and wide when in the box before the Swans replied with Mark Gower shooting wide following a well-worked move.
The Swans did have the ball in the net shortly after, with Wayne Routledge tapping home from Leroy Lita's low cross, but the winger was ruled offside.
But a minute before half-time, the Swans did have the ball in the net legitimately. After Lita flicked a pass to Moore, the latter nudged the ball past Wheater and outpaced the defender before scooping the ball over keeper Adam Bogdan.
That wasn't it, however, as there was still time for another goal.
With almost the last touch of the half, Bolton swung in a dangerous cross and Darren Pratley's header found the net despite Tremmel getting a hand to it.
Half-time: Bolton 1 Swans 1
The Swans started the second half the brighter of the sides, with Moore seeing his rasping 25-yard effort fly just wide of the upright before only a final heavy touch from Kemy Agustien's through ball was to deny him another chance to score.
But as the Swans were forcing their influence on the game, Bolton struck with a suckerpunch. Martin Petrov's angled shot from the left was spilled by Tremmel, and Eagles fired home from close range.
The Swans pushed on as they looked for an immediate response. And they went desperately close to doing so as Josh McEachran found Lita in the box, and his shot cannoned back off the angle of the post and crossbar.
Agustien's volley then bounced wide before Petrov's neat struck curled wide of the far corner.
The game continued to gather pace and Pratley went close again to scoring as his header dropped onto the crossbar before being cleared from danger.
Moments after, Pratley had another chance to adding to the hosts' lead as Jazz Richards' pass-back to Tremmel was short, and the midfielder latched onto it but pushed his shot wide.
Brendan responded by making two changes with Nathan Dyer and Danny Graham replacing Routledge and Lita after 66 minutes.
Bolton also made a change, England international Kevin Davies coming on in place of Ngog for the final 15 minutes.
The game was finely-balanced going into the latter stages, and Ashley Williams saw his header from Mark Gower's corner float over.
It proved Gower's last input as he was replaced by Joe Allen, while Coyle took off scorer Pratley and sent on Fabrice Muamba for the last 11 minutes.
Allen's first involvement was to find Garry Monk with a corner, but the skipper looped his header wide of the target.
The Swans then went inches wide of levelling as Agustien's superb cross found Graham, and the striker's header beat Bogdan but not the post as it deflected off the woodwork and David Wheater's knee before the keeper collected.