Darlington performed admirably against First Division opponents Sheffield United but it was Michael Brown who proved to be the scourge of Quakers.
The Hartlepool-born midfielder put in a great display on the left hand side in the second half and it was his cross which produced an injury time winner from French forward Laurent D'Jaffo.
Quakers can consider themsleves very unlucky not to have taken the Blades to extra time after a second half in which Gary Bennett's men enjoyed plenty of possesion and created chances they should have converted.
But Neil Warnock will feel his side derserved the win after dominating the first half and were only denied taking the lead by the heroics of Andy Collett who produced three top class saves, but Quakers were not disgraced and the Blades knew they had been given a tough game.
In contrast to last season when Gary Bennett rested several first-team regulars for the ties against Nottingham Forest and Bradford City, Darlington fielded a full-strength team albeit without the injured Neil Wainwright who was replaced by Mark Convery.
Also in the starting line-up was Saturday's super sub Richard Hodgson who came in for Brian Atkinson.
After just six minutes Darlington almost took a shock lead when Hodgson raced down the left and delivered an inviting low ball into the area but Danny Mellanby couldn't beat Blades' keeper Simon Tracey to the ball.
Both teams wasted golden opportunities to open the scoring in the 12th minute with first Hodgson stalling on the ball while in a good position in the box before losing possession, and then Paul Devlin blasted over for the Blades when he had more time than he realised.
As the 20 minute mark approached, Blades were beginning to stamp their authority on the game, creating plenty of chances, with Carl Asaba testing Andy Collett with a powerful drive and Shaun Murphy having a header tipped over the bar.
With ten minutes to go before the break the visitors were almost rewarded for their pressure when Paul Peschisolido turned smartly on the edge of Darlington's penalty area before shooting low towards goal but Collett made an excellent save.
In a rare break forward, Darlington wasted a good chance when Hodgson, who switched to the right, went to the by-line but instead of pulling the ball back to the unmarked Neil Maddison tried to pass to Mellanby on the six-yard line but he was crowded out.
The opening stages of the second period saw Darlington coping a lot better with their guests from the First Division and the first openings came Quakers' way with Conlon's close range effort going over the bar and then Murphy deflected agerous cross from the right into his keeper's hands.
Almost immediately Brown, who was barracked by the Feethams crowd all evening, beat three Quakers defenders before delivering a great cross to Peschisolido whose header was deflected for a corner.
Darlington should have scored the opener through Conlon when Brightwell picked out Mellanby who got behind United's defence on the left he stalled on the ball instead of laying the ball off to the unmarked ex-York striker who was in acres of space in front of goal.
A Darlington goal at this stage would have been deserved as they kept possesion for long periods but United's central defensive pair of Murphy and Santos kept Mellanby and Conlon well-marshalled.
After a short spell of United supremity during which Brown was a prominent figure as he used his trickery to deliver some excellent crosses, Hodgson was denied a penalty when he dribbled into the box before being shoved off the ball.
With ten minutes remaining Hodgson was again involved as this time he drove powerfully at goal after receiving a flick-on from Adam Marsh - on as a substitute for his first appearance of the season, following nice work by Conlon on the right.
Read more about Darlington FC here.
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