Ten man Wanderers exited the FA Cup at the fourth round stage following a 2-1 defeat by Liverpool at Macron Stadium.
The Whites had opened the scoring in the clash through Eidur Gudjohnsen from the penalty spot after Zach Clough had been fouled, but were then down to ten men after the dismissal of Neil Danns for a second bookable offence.
The Reds capitalised on their man advantage from thereon in and eventually drew level through Raheem Sterling with four minutes remaining before Phillippe Coutinho broke Bolton hearts in added time with a long distance effort which eluded Andrew Lonergan.
Zach Clough retained his starting place from the weekend’s draw with Wolverhampton Wanderers, while Dean Moxey and Eidur Gudjohnsen also made it into the side from the off for Wanderers.
The bench however boasted a number of youngsters, with Oscar Threlkeld, Georg Iliev and Tom Walker all taking their place amongst the substitutes.
The game began with gusto from both sides, but clear cut changes were few and far between inside the opening stages of the clash.
The visitors were to enjoy the first opportunity of the game with seven minutes on the clock, with Steven Gerrard’s strike from just inside the box through a crowded penalty area being comfortably saved by Andrew Lonergan.
Clough was the first Bolton man to test the Liverpool defence as he made a mazy run through midfield, but the young striker was ultimately halted in his tracks as he was just about to power inside the box.
Liam Feeney was next in the midst of the madness with his lofty ball into the area somehow eluding three Wanderers bodies, while Raheem Sterling’s angled strike was gathered by Lonergan at the second time of asking up the other end of the field.
Josh Vela and Gudjohnsen almost linked up perfectly with 15 minutes of the game gone as the midfielder found the Icelander unmarked twelve yards from goal, but the frontman put too much power behind his effort and saw it clear the crossbar.
With confidence growing and Wanderers pushing the Reds further and further into their own half, Wanderers came within inches of opening the scoring as Feeney found David Wheater’s head with a swinging free-kick, only to see Simon Mignolet get down low to deny the defender.
It was all one way traffic from the home side inside the opening quarter of the clash with Bolton enjoying the majority of the chances as Liverpool struggled to break down a stubborn Wanderers defence.
With Brendan Rodgers’ side having barely made tracks into Bolton territory, they nearly snatched the lead against the run of play with 13 minutes of the half to go as Sterling found himself in space just outside the six yard box, with the forward’s strike eventually coming off the post.
Matt Mills meanwhile, playing in a more advanced role up front, tried his luck from distance with a beautifully struck half volley which Mignolet had to be on his guard to collect.
As the half headed towards the break, Wanderers were again on the attack as yet another Feeney cross caused chaos amongst the Liverpool defence while Phillippe Coutinho attempted to beat Lonergan from distance but to no avail as the whistle went for half time.
With no changes for either side at the half time break, both teams came out for the restart visibly eager to be the first to find the back of the net and start the scoring in the tie.
The first real opportunity of the second period fell to Liverpool however, with Sterling finding himself with only the goalkeeper to beat as Dorian Dervite’s last ditch challenge whipped the ball from his feet with a goal seemingly imminent.
The visitors all of a sudden had Bolton on the backfoot, but the Whites’ defence was standing firming under pressure.
Out of nowhere though, Wanderers were handed the perfect opportunity to take the lead as Clough was fouled in the area by Martin Skrtel, with Gudjohnsen stepping up to calmly place the resulting spot-kick past Mignolet to send Macron Stadium into raptures.
Just what the game had been lacking, the match sprung into life from thereon in with Mills coming close for Bolton with a header with Feeney running riot down the right flank.
With 25 minutes remaining however, Wanderers were dealt a blow as Neil Danns was sent off for a second bookable offence.
Right from the madness however, Bolton almost had a second as Clough sprinted downfield, turned his man before unleashing an effort which rippled the near side of the net, while Gudjohnsen squandered a second as his close range header failed to trouble the Liverpool keeper with 20 minutes remaining.
With a man advantage however Liverpool pushed forward and were inches away from an equaliser as David Wheater headed Jordan Henderson’s strike onto the post with Lonergan beaten.
Sterling and Daniel Sturridge were next to come close for Liverpool, only to be denied by some last ditch defending while Henderson saw his effort from distance fly harmlessly wide.
Emre Can was next to rattle the woodwork for the visitors, with Lonergan’s palms denying the Liverpool man the equalising goal with seven minutes left.
Having pushed in their droves, Liverpool were finally rewarded with four minutes remaining as Sterling slotted home from close range after collecting Can’s volley into the box.
With five minutes of time indicated, Liverpool completed the comeback as Phillippe Coutinho curled home from just outside the box to send the visiting supporters into raptures.
There was still time for Wanderers to come close through Liam Trotter from close range while Fabio Borini forced the Bolton keeper into a smart save from close range, but there were no further goals as Liverpool progressed at the expense of the Whites.