Ipswich Town’s terrible run in the FA Cup continued as the Blues lost 1-0 on the road against Accrington Stanley at the Crown Ground.
Town have not won an FA Cup game since 2010 with their last victory a 2-1 win against Blackpool nine years ago, and they have now been eliminated from the competition by lower league opposition in three of the last four seasons.
In the first ever competitive meeting between Ipswich and Accrington, it was the home side who looked to catch the defence off guard as a corner came swinging into the centre of the box, but Freddie Sears cleared the danger after two minutes.
Town keeper Bartosz Bialkowski got bumped by Stanley striker Andy Mangan as he chased down a long ball and after an exchange of words, the referee restored order.
In the eighth minute, Paul Lambert’s men had their first meaningful attack with new loan signing Callum Elder, fresh from Leicester, linking up with Sears to make a run down the right but the 29-year-old wasted his delivery across goal.
Flynn Downes made a dart down the middle, only to see his burst of pace come to nothing as Accrington intercepted the ball and launched a counter-attack.
Stanley’s Sam Finley then unleashed the first shot on goal, which was comfortably collected by Bialkowski.
It was Gwion Edwards’s turn to try and spark a chance for Town and as the ball fell awkwardly in front of him, he released a wild drive into the Crown Ground car park with 18 minutes gone.
Bialkowski was made to work again soon after as Jordan Clark fired a low drive from the right but the Polish stopper was equal to it.
Tempers flared between the two sides after an altercation between Downes and Finley and for his intimidating reaction, the Brentwood-born youngster received a yellow card.
Approaching the half-hour mark, Clark caused problems for Town’s defence as he raced across the byline with quick feet until they were halted by a critical challenge from Toto Nsiala to clear for a corner, which came to no trouble.
Nsiala was forced to deny Clark again and the power of the Stanley midfielder’s shot was so vicious, the rebound inadvertently launched a counter-attack for Town, but Sears misread the path of the ball, as he ran underneath a high, awkward bounce.
In the 37th minute, Sears sprinted forward in search of support and he was joined by ex-Stanley striker Kayden Jackson, who followed the play through to Jon Nolan. Nolan had time and space for a strike from distance but again, the ball was way off-target.
At the other end shortly afterwards, Bialkowski was again forced to deny Clark as he tipped a low strike at his near post before keeping Town in the game again as he made a quick move to cancel out an attack from Finley.
Accrington were awarded a freekick with two minutes to the break after Downes and Clark collided in the middle of the pitch but that chance was given away by the home side with a high ball running out of play.
Sears desperately ran forward again on the right and cut inside to try and bend a shot into the far bottom corner but it was no problem for Stanley keeper Connor Ripley.
Accrington’s star-man Clark made the last move of the half to try and steal a half-time lead but his header fell wide of Bialkowski’s right post as the two sides went into the changing rooms goalless.
When play resumed, Town made a change as Downes came off for Teddy Bishop, and the 22-year-old had the first strike of the second half.
After Town’s freekick from the left was headed out, Bishop blasted a drive from distance, which curled wide to the left.
Bishop continued to make an impact as he surged forward and laid the ball off to the left wing, where Town earned a corner. Again, it came to nothing as a sea of heads deflected the ball out of Accrington’s area.
As the hour mark approached, Stanley attempted to catch Town out with route one football but Nsiala, was on hand to stop Accrington striker Billy Kee with a professional foul.
Bishop’s introduction much improved the visitors' style of play as he inspired more ball movement from across the midfield with two more attempts.
He dragged a left-footed effort across the face of the goal before failing to find the target from distance yet again.
Jon Nolan then found inspiration to have a go at pulling the Blues in front and his hard shot across the grass was parried away by Ripley with just over 20 minutes to play.
Town conceded a freekick in a dangerous position from the left in the 74th minute from which they fell behind.
Stanley captain Sean McConville posted a high arching ball to the far post, which was headed back across goal by Ben Richards-Everton for Kee to nod into an open net.
Sears burst into life again in the last 10 minutes to try and salvage an equaliser but he was denied a hero's goal once again by Ripley having been played in by Bishop.
The Blues pushed for an equaliser in the closing stages but once again their FA Cup campaign ends at the first hurdle, and as so often to lower league opposition. The Blues are now 14 games without a win in the competition they won in 1978.
Town's season of woe shows no sign of an upturn with their next fixture the visit of fellow strugglers Rotherham to Portman Road next Saturday.
Accrington: Ripley, Johnson, Hughes, Richards-Everton, Clark, McConville, Finley, Sykes, Mangan (Brown 66), Barlaser, Kee. Unused: Maxted, Williams, Mingoia, Perritt, Conneely, Watson.
Town: Bialkowski, Spence, Pennington, Nsiala, Elder, Nolan (Harrison 80), Edwards, Downes (Bishop 46), Dozzell, Sears, Jackson (Keane 66). Unused: Gerken, Chambers, Kenlock, Lankester. Referee: Dean Whitestone (Northamptonshire) . Att: 2,869 (Town: 1,224).