Birmingham 2 Bolton 3
A Chung-Yong Lee goal one minute from time ended Birmingham's hopes of a second trip to Wembley this season as Bolton triumphed in the FA Cup sixth round.
A Chung-Yong Lee goal one minute from time ended Birmingham's hopes of a second trip to Wembley this season as Bolton triumphed in the FA Cup sixth round.
The Trotters had twice taken the lead through Elmander and Kevin Davies but, each time, Blues clawed level first through Cameron Jerome and then Kevin Phillips.
A replay looked inevitable but the substitute Lee settled matters with a close-range finish to send his side to a Wembley semi-final.
Birmingham manager Alex McLeish made five changes to the injury-ravaged side which drew at Everton on Wednesday with Stuart Parnaby, Curtis Davies and David Murphy replacing usual defensive stalwarts Liam Ridgewell, Roger Johnson and Stephen Carr.
In midfield, Sebastian Larsson, Jordon Mutch and Jean Beausejour retained their places from the midweek game, while Barry Ferguson made his return to the side in place of Lee Bowyer.
Up front, perennial substitute Kevin Phillips was chosen to partner Jerome, who also started at Goodison Park.
But it was on the bench where Blues lack of cover was most greatly exposed.
Inexperienced teenager Nathan Redmond and reserve defender Alpaslan Ozturk took their places alongside Derbyshire, Ridgewell and Craig Gardner, who was also returning from a dead leg sustained in the Carling Cup final.
The Trotters' included former Blues midfielder Fabrice Muamba in the starting line-up, while fellow former Blues player Robbie Blake took his place on the bench.
Other familiar faces lining up for the visitors included former Villa defender Gary Cahill in defence and ex-Albion defender Paul Robinson.
The ground was surprisingly packed at kick-off with Bolton virtually filling the Railway end.
And it was the away side that forced the game when Muamba poked a tame shot straight at goalkeeper Ben Foster four minutes in, after good work from Davies and Stuart Holden.
Elmander then headed over from a Martin Petrov corner, before Curtis Davies nodded a tame header into goalkeeper Jussi Jaaskelainen's hands from a Larsson corner
Gretar Steinsson became the game's first booking after 19 minutes after body-checking Phillips, who was looking to launch a counter attack on the right wing.
But Elmander opened the scoring 21 minutes in slotting home Klasnic's flick-on, from Muamba's header.
Things got worse for Blues when McLeish was then forced to swap one injured player for another, as Martin Jiranek was replaced by Liam Ridgewell 27 minutes in.
The Czech international then went down injured after a collision with Holden early in the game, presumably further aggravating the ailment, while Ridgewell has been playing with a groin strain.
Ferguson, who is recovering from a broken rib, was then replaced by Redmond three minutes later, with the teenager receiving a great reception.
But Blues' fortunes improved when Jerome drew them level seven minutes before the break.
The striker smashed home David Wheater's mis-cued clearance from the edge of the box to the clear delight of his manager, as well as the home supporters.
Bolton felt aggrieved early in the second when Curtis Davies handled the ball in the area.
But referee Phil Dowd waived away penalty appeals, insisting Cahill had pushed the defender to force the error.
There was controversy at the other end when Jerome went down in the box from Jaaskelainen's challenge, after Redmond had put him one-on-one but, again, Dowd again waived appeals away. Replays suggested he was correct on the latter.
Bolton boss Owen Coyle replaced Ivan Klasnic with Lee and Muamba with Mark Davies 61 minutes in, with the substitute making an immediate impact by clearing Phillips'goalbound header.
Muamba also appeared to have set up Bolton's second goal seconds later, when his pass found Elmander and the blocked shot was turned past Foster by Kevin Davies.
Davies was flagged offside but made amends a minute later, both winning and scoring a legitimate penalty.
The forward was tripped by namesake Curtis Davies with his back to goal, after the defender had allowed a long-ball pass to bounce dangerously in the box.
The Bolton striker tucked away the gift low into Foster's right hand corner to edge Bolton closer to Wembley.
Elmander then missed a great chance to seal his team's passage to the semi-finals, completely missing Lee's superb right-wing cross.
Phillips almost punished the error when he rattled the post from distance with 20 minutes remaining.
Foster then kept Blues in the game when he denied Elmander, who had gone clear deep inside the box.
Phillips appeared to have rescued the tie with nine minutes remaining, exquisitely lobbing Jaaskelainen from outside the box.
It was a genuinely world class finish, from Redmond's flick on, after Curtis Davies had headed the ball downfield from deep in Blues' own half.
Kevin Davies was then booked a minute later for a challenge on Ridgewell, as McLeish swapped Murphy for Matt Derbyshire in a bid to avoid a replay.
His plan worked, but not in the way he'd planned, as Lee burst through to turn home Davies' cushioned header in the final minute to take Bolton to Wembley.