The epic spot-kick contest, which finished 9-8 to the visitors, followed a goalless 90 minutes in which United spurned several presentable chances to seal victory.
Following on from victories over Bury and Oldham, the Reds were bidding for a third straight victory in this season’s group stage. Having overcome Bolton in last year’s final at Old Trafford and recently hammered the Trotters in the league, Ole Gunnar Solskjaer’s side were up against familiar opposition.
Visiting goalkeeper Adam Bogdan was forced into a smart save by Angolan international Manucho, who had earlier headed over the bar, while Danny Sissons almost caught out Ben Amos in one of Bolton’s rare forays forward.
An even first-half ended goalless, but Bolton-born Sam Hewson, already a scorer against the Trotters this season in the league, spurned a glorious chance shortly after the interval.
Tom Cleverley, another United midfielder with goalscoring previous against the Trotters, then worked Bogdan again, but the Reds were indebted to a linesman’s flag when Sheridan’s goal was ruled out for the visitors.
In the event of a draw, Senior Cup group matches are always decided by penalty shoot-outs. Incredibly, 14 successful conversions had the score locked at 7-7 when David Gray’s kick was saved. United were let off when Nathan Woolfe blazed over but there was no such reprieve when Anton Bryan also missed, allowing Tom Eckersley to seal the points for Bolton.