Isaac Ogundere converted the decisive penalty in a 4-2 shootout victory.
Johnnie Jackson labelled AFC Wimbledon’s penalty shootout triumph over Premier League Ipswich as the highlight of his managerial career.
Former Wimbledon striker Ali Al-Hamadi gave the visitors the lead but Omar Bugiel hit back for the Dons five minutes before the break.
Matty Stevens thought he had fired his side into the third round after heading into the top-left corner but Conor Chaplin capitalised on an Owen Goodman error to get The Tractor Boys back on level terms four minutes from time as the match ended 2-2.
Crystal Palace loanee Goodman made amends, saving two spot kicks before Isaac Ogundere converted the decisive penalty in a 4-2 shootout victory.
The Dons will play Premier League side Newcastle in the third round.
Jackson said: “I think it is probably the highlight so far I would say [of his managerial career].
“Certainly one of them anyway. That is the third time coming up against Kieran [McKenna] as a manager and it has not gone great for me in the previous couple.
“So to win tonight against such a talented young coach is nice on a personal level and I am just really pleased for the football club to have a night like this.
“For us as a football club to have a night like this, beating a Premier League team, it is outstanding.
“Obviously my old striker popping up with a goal after three minutes, you think oh hell, you knew that was going to happen.
“For 15 to 20 minutes they had their way with us and I was a little bit concerned that the game might get away from us.”
Ipswich’s starting eleven featured six debutants, including Manchester City loanee Kalvin Phillips.
McKenna insists it was the correct decision to give new players minutes, with the Premier League season in mind.
“I think it was the right thing to do,” he added.
“Of course, going out of the cup competition is not good and we are disappointed for the supporters who have come here tonight and given us really good support.
“We wanted to progress in the competition but it is really really clear what our priorities are this season.
“We have got a lot of new players to integrate and not many chances to do it.
“It is not possible to do it in a Premier League game so to get as many of them on the pitch tonight as we could was the priority for the football club.
“Of course, that always gives the chance that the performance won’t be as cohesive as you would hope and that is what brought the uncertain elements to the game.
“A perfect start, to be honest there were some really positive things about the performance.”
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