Wolves again took a Johnstone’s Paint Trophy tie to penalties – but they deservedly succumbed to a superior Notts County side.
League One strugglers County secured a place in the area quarter-finals with a 3-1 victory on spot kicks.
Successful penalties from substitute Danny Haynes, Joss Labadie and one-time Wolves trialist Mark Fotheringham did the trick as Kenny Jackett's side failed to repeat their shootout win over Walsall in the last round.
Leigh Griffiths netted his, but Bjorn Sigurdarson and Kevin Foley then fired over from 12 yards before James Henry’s effort was saved by keeper Fabian Spiess on a night to forget for the home side in front of Molineux’s smallest crowd for many years, 7,166.
Booed off at half-time, a strong Wolves team were only kept in the game by a string of saves from man of the match, keeper Carl Ikeme, who kept his fourth successive clean sheet.
Ikeme denied Adam Coombes twice, Yoann Arquin twice and Andre Boucard as Wolves were often sloppy in possession and lacking cohesion until the latter stages of the game.
Head coach Kenny Jackett made four changes to the side that beat Colchester 3-0 on Saturday.
And with six players called up for international duty and Bakary Sako recovering from illness, Jackett picked almost the strongest side he could.
Foley, Ethan Ebanks-Landell, George Elokobi and Jake Cassidy replaced Matt Doherty, Danny Batth, Sam Ricketts and Kevin Doyle.
Doherty, Ricketts and Doyle were on international duty, although Ricketts has subsequently withdrawn from the Wales squad with a knee injury, while Batth was on the bench, which had academy keeper Jonathan Flatt involved for the first time at senior level.
Richard Stearman captained the side for the first time this season and the Wolverhampton-born defender led the Broadbent family laying flowers behind the Stan Cullis Stand goal as the sparse crowd joined in a minute’s applause in tribute to the late, great Peter Broadbent before kick-off.
Wolves fans endured a pretty dreadful first half, after which the players were booed off.
Jackett’s side had the first sight of goal in the second minute but Cassidy’s quickly-despatched fierce shot flew a few wide of the left-hand post.
From there though however, Notts went on to comfortably outperform Wolves for the first half.
Dangerous striker Arquin headed firmly over the bar from a third-minute free kick before Ikeme made the first of a flurry of saves when he flew out of his goal to deny Coombes three minutes later.
County caught Wolves napping with a quickly-taken free kick on 14 that saw Arquin cut inside for a curling shot beaten away by Ikeme.
Wolves’ first and only serious chance of the first half came in the 16th minute when Griffiths curled a 30-yard free kick inches wide after he was tripped by midfielder Fotheringham, which earned the former Wolves trialist a booking.
County remained on top and Jamal Campbell-Ryce was next to try his luck from 22 yards which flew a few feet wide.
Gradually, Wolves got worse as their passing game looked more and more pedestrian, less productive and more sloppy.
And it was no surprise when they were booed off at the break.
Wolves brought on Bjorn Sigurdarson at half-time for Elokobi in a switch that saw Scott Golbourne move back to left-back and Henry switch from right wing to the left side, with Sigurdarson at wide right.
But the reshuffle paid little dividends to begin with as County missed another chance in the opening seconds of the second half.
Again Ikeme came to the rescue for Wolves, this time racing out to block Coombes’s effort with his legs.
Wolves at least upped the tempo in the second period, but it was Notts who continued to create the openings.
Ikeme rescued Wolves again in the 54th minute Joss Labadie put Arquin through and the keeper smothered his shot, Ebanks-Landell putting off Coombes from the rebound.
In a more open and committed second half, Mustapha Dumbuya saw his shot deflected wide after cutting inside on the hour.
But Wolves produced their best move of the match in the 67th minute as Griffiths, Henry and Golbourne combined for the latter to cross which was hacked away from in front of the line, although replays showed the ball was going wide anyway.
Griffiths brushed the sidenetting with a free kick after he was fouled again on 69, but despite looking more dangerous in the closing stages, Wolves couldn’t find a way through in normal time as County had the final on-target attempt when Andre Boucaud’s 25-yard drive was scrambled away by Ikeme.
And the penalties went the right way as County celebrated victory.