Town's Carling Cup campaign once again came to an early end at the hands of lower league opposition as the Blues were defeated 5-3 in a penalty shoot-out by the MK Dons after a 3-3 draw at stadium:mk.
Jim Magilton fielded the same eleven which defeated Sheffield Wednesday so comprehensively on Saturday in stadium:mk's first cup tie.
The game's first serious goalmouth action came in the 13th minute. Mark Wright crossed from the right and an unmarked Leon Knight headed powerfully against the bar. Neil Alexander stopped Jon-Paul McGovern's headed follow-up.
But the home side weren't to be denied a goal for too long after starting more brightly and with more urgency than Town. Alan Navarro laid the ball back from the right and Knight slammed it home from eight yards.
Pablo Couñago was unhappy with Sean O'Hanlon catching him in the face with an arm in the 16th minute, but after treatment carried on. Soon after returning, the Spaniard made a clever turn inside the area, but his shot was headed out for a corner.
However, it was the Dons who would score the game's second goal. McGovern wafted in a cross and Alex Bruce inexplicably looped the ball over Neil Alexander and into the net for one of the most surprising own goals in Town's history.
As the half hour approached, Navarro was booked for a foul on Couñago, Jason De Vos heading Garvan's freekick straight at Dons' keeper Nathan Abbey, who was on a short-term contract with the Blues four seasons ago.
Jon Walters shot across the face of goal before Couñago saw a shot blocked after a one-two with the former Chester man.
By now Jim Magilton was down on the touchline having started the game from the stand, clearly unhappy at the way the match was progressing.
In injury time, the Blues were given a lifeline from the penalty spot. Abbey twice saved from Alan Lee with the loose ball rebounding out to Gary Roberts, who took it past Navarro before crashing to the ground. Contact looked minimal even if the lunging challenge was ill-advised inside the area.
But referee Paul Taylor awarded the penalty and Alan Lee netted his third goal of the season.
Town had been distinctly second best throughout the opening period and deserved to go in a goal down. Gary Roberts was replaced after a less than effective half, Danny Haynes taking over.
Jim Magilton's teamtalk seemed to energise his side and the Blues were quickly on top as the second period began, although there was a lucky escape when De Vos cleared a Knight backheel after Alexander had failed to hold on to the ball.
Town got back on terms after a powerful run from Jon Walters from halfway ended with him laying the ball wide for Pablo Couñago, whose cross was put into his own net by Kieran Murphy.
For five minutes or so the Blues were rampant. Haynes shot just over, then Walters had an effort deflected for a corner, which De Vos stabbed against a defender on the line. Bruce, perhaps hoping to make amends for earlier, volleyed over.
For the home side, Knight volleyed an enormous Jude Sterling throw-in over from eight yards, then the former Brighton man stabbed a rebound against the post after Alexander had saved from O'Hanlon. Town's goal was living a charmed life and the Dons were once again looking the hungrier side.
A quick Haynes break might have ended in a goal, but Couñago couldn't find room for his shot. At the other end, Alexander pushed a Knight shot wide. Murphy headed the corner over, the Dons continuing to have much the better of it in the air from set pieces.
Dan Harding was booked for dissent after complaining about a linesman's award of a throw-in, although he may have had a point and it was clear that the Town players were becoming increasingly frustrated with Mr Taylor's overfussy performance.
On 68 Alan Lee teed up Tommy Miller on the edge of the box, but the midfielder's shot was deflected wide.
Alexander saved from Lloyd Dyer, then Luke Howell hit the post with a shot from the edge of the area. Jim Magilton decided that changes were required and replaced Couñago with Billy Clarke and Lee with Sylvain Legwinski, Garvan moving to a left midfield role with Clarke on the left and Walters and Haynes up front.
With nine minutes remaining, Clarke was yellow-carded for what looked like a perfectly good tackle, before Walters came very close to getting a toe to a Garvan cross.
The Town number 19 then shot across the face as the Blues finally began to wake up again. Haynes forced two saves from Abbey, the second with an impressive overhead kick, and the keeper also stopped a Clarke shot in at his near post.
Legwinski's 25-yard shot was saved, prior to O'Hanlon heading another Sterling long throw over the bar. Referee Taylor blew his whistle to signal extra-time.
Abbey made a fine save from Clarke's curling effort on 92 as Town started the additional half hour strongly.
The Blues finally took the lead in the 98th minute when Owen Garvan netted the first header of his career, getting on the end of Danny Haynes's cross from the right at the far post.
Abbey almost conceded a Bryan Gunn-style own goal two minutes later but got back to clear his lines.
Despite having gone behind, the home side weren't giving up and it took a superb saving challenge from De Vos to prevent Knights from scoring.
After the turnaround, sub Kevin Gallen sent a freekick over the bar, prior to referee Taylor awarding a penalty for an offence which was a complete mystery to Town fans at the opposite end of the ground. The Town players protested against the award, apparently for a push by Jason De Vos, but to no avail and Gallen sent Alexander the wrong way from the spot.
There was just time for Clarke to shoot wide before the whistle blew for the end of the 120 minutes.
Town continued their woeful record in penalty shoot-outs — one win in nine — as Dyer, Wright, Gallen, Sterling and O'Hanlon all scored for the home side. Clarke, Walters and De Vos were successful for the Blues, but Harding's fourth for Town was stopped by Abbey.
Once again a disappointing Carling Cup performance from the Blues with the League Two side looking more up for it from the start and Town only really coming into the game for spells just before and after half-time and towards the end.
Neither penalty appeared to be a correct decision, but the mistakes typified a poor and frustrating display from referee Taylor.
Town weren't much better, although Jon Walters had another fine game in his new wide role. Sylvain Legwinski's introduction gave the side a more solid look and the Frenchman could well be pushing for a start against Plymouth on Saturday.
Defensively, the Blues looked likely to concede at any set-piece, admittedly against a significantly taller side, and Leon Knight's pace caused no end of trouble in the first half. Only some excellent last-ditch tackles from De Vos in particular and several clearances from the goal-line prevented a defeat in normal time. A far better performance will be required at Home Park.
Town: Alexander, Wright, Harding, De Vos, Bruce, Garvan, Miller, Roberts (Haynes 46), Walters, Lee (Legwinski 75), Couñago (Clarke 75). Unused: Supple, Wilnis. Att: 7,496.
Get the fastest and most comprehensive Ipswich Town news service at ipswichtown.footballlatest.co.uk.