Blackpool were made to rue a penalty miss during normal time as they were dumped out of the Checkatrade Trophy on spot kicks by Wycombe.
Will Aimson’s effort, which came back off the post, handed the Chairboys a 5-4 win on penalties to seal their progression through to the quarter final stage.
But Pool were forced to rue a missed penalty during normal time, after Danny Philliskirk’s weak effort was saved when his side were already 1-0 up courtesy of Kelvin Mellor’s header.
The game, played in front of a virtually empty crowd at Bloomfield Road despite a generous figure of 766 given out as the official attendance, started at a slow pace and it took almost 10 minutes for the first sight of goal, with Mark Cullen drilling across the six-yard box with no teammates there to tap home.
But the following attack brought a goal for the Seasiders, with full back Kelvin Mellor taking advantage of slack Wycombe defending to nod a downward header into the back of the net from Mark Yeates’ deep cross.
The goal came with minimal effort but it presented Mellor with his fifth goal of the season.
The visitors had made a sloppy start to the game but they almost found an instant leveler when Luke O’Nien rattled the bar with a drilled effort from the edge of the bar.
Pool ‘keeper Sam Slocombe was left watching on as the midfielder’s effort, which looked destined for the top corner, flew onto the woodwork.
The woodwork was left shaking once again just a minute later when Kelvin Mellor’s cross was inadvertently deflected onto the post, with ‘keeper Jamal Blackman left stranded.
Blackpool’s early goal seemed to spring Wycombe into life, and the Chairboys should have been level when Paul Hayes was presented with a half volley when left unmarked in front of goal, only to side foot wastefully over the bar.
The hosts then raced up the other end and Armand Gnanduillet had his own gilt-edged chance, but despite getting clear contact on his volley it went disappointingly over the bar.
Pool changed their formation for the third game running, with Mark Yeates and Bright Osayi-Samuel - usually used to being deployed as wingers - playing in unfamiliar central midfield roles as part of a diamond formation.
But the duo showed composure and discipline and they linked up well with those ahead of them.
The Chairboys thought they had an equaliser when they had the ball in the back of the net through Garry Thompson’s close-range effort, only for it to be ruled out for offside.
And a minute later it looked as though they would be punished, with the Seasiders being awarded a soft penalty when Osayi-Samuel was felled in the box by Marcus Bean.
But Danny Philliskirk, clearly low on confidence, saw his tame effort easily saved by Blackman.
It was his second penalty miss of the season, after a similarly weak effort against Cambridge earlier in the season.
Mark Cullen, who would have been a leading candidate to take the spot kick, then went close soon after the penalty miss but he couldn’t quite get a shot away.
The Tangerines remained on the front foot for the latter stages of the first half but struggled to create any more clear chances.
The Seasiders started the second period in a similarly positive mood with half-time substitute Jack Redshaw looking dangerous.
Michael Cain stung the palms of Blackman when trying his luck from range, with the highly rated Chelsea loanee spilling the ball into his six-yard box before collecting at the second attempt.
The visitors began to grow into the game as the second half wore on, with referee Eddie Ilderton waving away half-hearted penalty appeals after the ball was slammed against Kelvin Mellor’s hand from merely a yard away.
Will de Havilland then looped a header that dropped narrowly over Slocombe’s bar after a hopeful cross into the Blackpool box.
They had an even simpler opportunity when Sam Wood was left unmarked in front of the Blackpool goal, only to head wide of goal under no real pressure.
But their pressure eventually told when, with just 10 minutes remaining, Anthony Stewart rifled in at the back post after latching on to near post flick.
Pool’s defending was lax as they were punished for failing to clear their lines.
It has to be said the goal had been coming, with the away side looking like the only side intent on creating opportunities in the second period.
Although the equaliser did spark Pool back into life, it was Wycombe who came closest to a late winner with Stewart inches away from his second of the game after letting fly from the edge of the box.
With five minutes of stoppage time added on, both sides pressed for a late winner but the defences held firm.
It meant the tie would be decided by a penalty shootout, with Will Aimson missing the only spot kick to seal the win for the away side. Danny Philliskirk's penalty, his second of the game, was saved by Blackman but extraordinarly bounced back and over the line.
Blackpool: Slocombe, Mellor (des Pres), Robertson, Aimson, Pugh, Cain, Philliskirk, Yeates, Osayi-Samuel (Payne), Cullen (Redshaw), Gnanduillet
Subs not used: Lyness, Aldred, Roache
Wycombe: Blackman, Stewart, Jacobson, De Havilland, Müller, Bean, O'Nien, Wood, Thompson, Hayes (Akinfenwa), Weston (Cowan-Hall)
Subs not used: Richardson, Jombati, McGinn, Freeman
Referee: Eddie Ilderton
Attendance: 766 (53)