Holders Maidstone beat Dartford 8-7 on penalties to reach the semi-finals of the Kent Senior Cup.
After 15 perfect spot-kicks, Stones keeper Josh Strizovic denied Dan Johnson to send United through.
The game went straight to penalties following a 1-1 draw that saw Darts forward Ben Greenhalgh play almost the entire second half in goal after Bailey Vose, who earlier saved an Ollie Muldoon penalty, was sent off for bringing down Elliott Romain.
Darts were leading 1-0 at the time, thanks to Charlie Sheringham’s first-half spot-kick, but Romain scored a late equaliser.
Simon Walton was in sole charge of the Stones after Tristan Lewis left on Tuesday afternoon, with the appointment of a new manager imminent.
The caretaker boss offered plenty of encouragement from the sidelines but it was a fairly low-key affair in the first half.
Dartford took the lead with a 24th minute spot-kick after referee Constantine Hatzidakis ruled Lee Noble’s free-kick had been blocked by an arm in the wall.
Sheringham stepped up and beat Strizovic down the middle.
Muldoon’s 25-yard free-kick clipped the bar moments later.
He had a better chance to level five minutes before the break after ex-Maidstone defender Callum Driver fouled Romain in the box but Vose saved his penalty.
Vose’s evening was over after racing out of his area and bringing down Romain three minutes into the second half.
With no sub keeper, Greenhalgh took the gloves but Maidstone didn’t test him until midway through the half when he made a double save in a goalmouth scramble.
The equaliser arrived in the 81st minute when Jack Paxman squared for Romain, who rolled the ball into the far corner.
Greenhalgh just about kept out Jarvis Edobor’s long-range strike as Maidstone pushed for a winner.
Then Jack Powell and Paxman set up another good chance for Romain but Tom Bonner made an excellent block in front of Greenhalgh.
Darts almost nicked it in the first minute of added time when Kudus Oyenuga ran on to Sheringham’s pass and hit the underside of the bar.
Jack Powell, Muldoon, Paxman, Romain, Dan Wishart, Aryan Tajbakhsh, Jamie Philpot and Will De Havilland scored for Maidstone in the shoot-out.
Sheringham, Billy Crook, Elliot Bradbrook, Ronnie Vint, Oyenuga, Lee Noble and Tom Bonner netted for Darts before Strizovic saved from Johnson.
Dartford: Vose, Driver (Wynter 90mins), Vint, Bonner, Greenhalgh, Noble, Darbyshire (Crook 58mins), Bradbrook, Hayes (Oyenuga 58mins), Johnson, Sheringham. Subs not used: Roberts, Coker.
Maidstone: Strizovic, De Havilland, Wassmer, Edobor, Paxman, Muldoon, Tajbakhsh, Taylor (Powell 70mins), Richards (Wishart 61mins), Romain, Philpot. Subs not used: Robinson, Phillips, Ross.