Wanderers' Bloomfield Road curse continued as they bowed out of the Bristol Street Motors Trophy 5-4 on penalties.
Zac Ashworth missed the crucial spot kick after a tense and scrappy encounter, meaning Bolton will not get their chance to defend their prize at Wembley in April.
They have not won at Blackpool’s HQ since 1977 but will now have to wait until three points are at stake in February to do so at the 16th attempt.
Wanderers made eight changes from the side that had won at Carlisle, their three central defenders the only players who survived from the starting line-up at Brunton Park.
Among the changes, Liverpool loanee Calvin Ramsay was given his debut, there was a first start for Nat Ogbeta and Carlos Mendes Gomes was selected from the off for the first time since early December.
Cameron Jerome should have put Bolton ahead after only a few minutes, seizing on to Jon Dadi Bodvarsson’s flick and outmuscling Callum Connolly, he fired straight at keeper Richard O’Donnell.
Ramsay quickly showed what he was going to bring, bursting on to a loose ball from Andy Lyons to whip a dangerous cross in from the right that demanded a finish.
The Scot showed plenty of classy touches, linking up especially well with Mendes Gomes, and didn’t waste the ball, all of which are good omens for the next few months.
Precision was lacking in the centre of midfield, however, with both George Thomason and Aaron Morley showing a little ring-rustiness. The latter’s mis-placed pass 10 minutes in allowed Ollie Norburn to slip a pass through for Sonny Carey which looked to have put him clean through on goal, especially after Ricardo Santos slipped on half-way. The Bolton skipper turned on the afterburners, however, and made a fine saving challenge.
Both middle men started to pick up, and Thomason brought another save out of O’Donnell, whose parry was then headed behind by Lyons just as Bodvarsson closed in.
Ramsay continued to be a good out-ball down the right for Wanderers, and worried the Blackpool keeper once again with a speculative shot that nearly crept inside the near post.
Thomason was warming up, launching himself into, and winning, two successive challenges on the edge of the Tangerines box. Suspended for Saturday’s game at Barnsley, he had more reason that most to leave everything on the pitch.
Blackpool did get the ball the in the net as Jordan Gabriel got around Joel Coleman to score but celebrations never got an opportunity to start as the linesman raised his flag for offside.
Moments later the officials took centre stage again, this time referee Seb Stocksbridge issuing only a yellow card to Connolly after he had wrestled down Bodvarsson, who had turned him on half-way. The 26-year-old, once a loanee at Bolton, looked a little fortunate at first glance that a harsher punishment was not dished out.
Morley’s radar was starting to function by the close of the half and he picked out Jerome with a fine free kick, nodded back at the far post to force Matt Pennington into a panicky clearance on his own line.
Wanderers finished the half strong, Mendes Gomes was searching out possession on either side of the pitch, and nearly made O’Donnell pay for a mis-kick right on the stroke of half time.
And then perhaps the talking point of the night. Santos had gone back into the dressing room early from the warm-up pre-match, so when he failed to appear for the second half, warning bells sounded, especially with just two days left of the transfer window.
Josh Dacres-Cogley replaced his skipper – who had picked up a yellow card – and played on the right side of the back three with Eoin Toal reverting to the central role.
Blackpool enjoyed their best spell of the game so far after the break, with Karfamoko Dembele unlucky to see his snap shot bounce off a Bolton defender and Shayne Lavery having another goal chalked out for a foul on Coleman.
With both sets of fans in raucous mood, the home side continued to press. Pennington nearly finished off a move he started with a run from deep, squeezing a shot narrowly wide.
Wanderers changed personnel again with Zac Ashworth and Kyle Dempsey coming off the bench, which meant Mendes Gomes being shifted over to wing-back.
All the pressure at this point was coming from the home side. Norburn’s shot from the edge of the box forced Coleman into a scrambling save.
Home subs CJ Hamilton and Kylian Kouassi then combined well, the former squeezing a shot just wide of the near post.
Wanderers were struggling to keep possession and get a foothold in the game, the travelling fans calling for Dion Charles to get his chance from the bench. On 74 minutes they got their wish.
As time ticked down the urgency increased. Hamilton nearly embarrassed Coleman, who got himself stranded trying to clear a long ball down the right. The mainstay of Blackpool’s scant but vocal support watched helplessly as his shot into the empty goal curled wide.
Bolton started to live a charmed life. Jack Iredale allowed a long ball to bounce and Kouassi nearly nipped in ahead of Coleman.
Chances had been few and far between in the second period but with eight minutes to go Dempsey and Bodvarsson combined to cut a ball back for Thomason – dreaming of a repeat of his winning goal in the league. Unfortunately, on this occasion, his side-footed effort cleared the bar by some distance.
Thomason then brought the travelling fans to their feet with a scything challenge on Gabriel in front of the away stand, punished by his obligatory booking. Tempers flared, and Bolton suddenly found some impetus.
The Whites so nearly found a winner when Charles turned to drive Dempsey’s cross at goal – O’Donnell finding himself in exactly the right spot, as he had done throughout the first half.
And so it went to spot kicks. Blackpool won the toss and directed traffic to their end.
Hamilton and Morley traded the first, but when Connolly scored Blackpool’s second, Charles saw his effort saved by O’Donnell.
Just as in the game itself, the keepers got on top. Joel Coleman saved from Bolton-born Ollie Norburn and then again from Gabriel but Bodvarsson also had his effort turned away.
Mendes Gomes scored and Coleman very nearly denied Dembele.
Thomason, Kouassi, Dacres-Cogley and Pennington also found the mark until young Ashworth walked up for the 14th penalty of the night. Stopping to tie his shoelace on the edge of the box, the portents were not good.
Placing his shot just wide of the post, Blackpool’s supporters went stratospheric.
Wanderers’ followers burst instantly into song. Paraphrasing their sentiment, forget the cup, we’ll win the league.
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