Exeter goalscorer Troy Brown was part of the Ipswich side when the two teams last met at this stage of the League Cup in 2010
League Two Exeter City beat Ipswich Town 4-2 on penalties as they overcame a Championship side for the second time in three seasons in the Carabao Cup.
Kayden Jackson's low cross from the left byline squirmed under City keeper Christy Pym to give Town the lead.
Former Ipswich youngster Troy Brown levelled from close range as the game ended 1-1 after 90 minutes.
Trevoh Chalobah put Ipswich's fourth kick wide, allowing Lee Martin to score the winning penalty for Exeter.
Ipswich made three changes to their line-up, while Exeter made four as the the League Two side more than held their own against their higher-ranked opposition.
Former Ipswich midfielder Lee Martin had a chance to put City level just before half time, while team-mate Archie Collins hit the side-netting soon after the restart.
Both sides had opportunities to win the game after Brown's equaliser, but it was Pym who atoned for his mistake for the Ipswich goal as he saved Teddy Bishop's opening penalty after Exeter skipper Jake Taylor had missed City's first.
Exeter were faultless from then-on as Pierce Sweeney, Tristan Abrahams and Collins all scored, while Luke Chambers and Jackson converted for Ipswich before Chalobah's miss.
The Devon side last reached the second round two years ago, where they lost to then-Premier League side Hull City having beaten Brentford at St James Park in the first round.
