Exeter City booked their place in the second round of the Carabao Cup with a 4-2 penalty shootout win following a 1-1 draw at St James Park.
Kayden Jackson's first half goal was cancelled out by Troy Brown's header after the break before Lee Martin netted the decisive penalty to send the Grecians into the next round.
Manager Matt Taylor made four changes to the side that started the victory at Morecambe last weekend, with Craig Woodman, Jordan Tillson, Lee Martin and Matt Jay coming into the side.
It was a cagey opening 10 minutes with both sides having spells on the ball without testing either goalkeeper.
But it was the Grecians who caused the first real scare of the match when Jay did wonderfully to cut inside and deliver a dangerous looking cross towards Jayden Stockley, but the ball was just cut out in time by the Town defence.
The clearance could only find Lee Martin, though, and he did well to cut onto his left foot before shooting towards the far corner, but for Aristote Nsiala who made a vital block as Town eventually cleared their lines.
Moments later Trevor Chalobah almost fired the away side ahead when Jonas Knudsen’s cross was cleared to the edge of the box before the midfielder hit a first-time volley just wide of Christy Pym’s goal.
As the half continued, Paul Hurst’s men began to dominate possession and they almost went ahead when Janoi Donacien got in down the right before shooting from a tight angle.
The onrushing Pym did well to get a hand to it as he punched the ball away with the help of Pierce Sweeney who cleared it out of the City area.
The Grecians then had a wonderful opportunity to go ahead when Sweeney’s ball into the path of Stockley saw the forward set Lee Martin away down the right-hand side. The midfielder then squared it into the path of the sliding Jay, but the striker couldn’t connect cleanly as his effort edged just wide.
Craig Woodman then had another attempt just after the half hour mark when a City free-kick was cleared before the left back volleyed right footed just over Bartosz Bialkowski’s goal.
But it would be the Tractor Boys who would prove more clinical when a City move forward broke down and the away side counter-attacked down the left-hand side.
Jackson then darted into the box before shooting ambitiously towards the near post catching out Pym as the Championship side took a lead into half-time.
Matt Taylor then made two changes on 52 minutes with Archie Collins and Tristan Abrahams introduced. The former almost made an instant impact when he profited from a Hiram Boateng tackle before he drove at the Town defence to see his powerful shot blocked for a corner.
A good spell for City then saw Boateng get down the left as he latched onto Woodman’s quick throw before crossing for Abrahams, who was in a good position, but the youngster mistimed his effort as the ball rolled under him.
And that good start to the second period for City paid off when they levelled just after the hour mark. Substitute Jack Sparkes’ low free-kick from the right was flicked on by Jake Taylor before Brown nodded the ball over the line from a couple of yards out.
The visitors rarely threatened Pym’s goal for much of the second period, but did create a good chance on 75 minutes, again prospering from a counter-attack. After they broke at speed the ball was pulled back to Jon Nolan on the edge of the City box, but he could only shoot over into the Big Bank.
Sparkes was next to try his luck at the Town goal when he tested Bialkowski with a close range free-kick just minutes before Pym was forced into a smart save from Adetayo Edun, as the game edged towards a penalty shootout.
But another golden chance then fell for City four minutes from time when the Grecians broke through Lee Martin before he played in Abrahams, whose first time shot with his left foot was saved well by Bialkowski.
Ipswich then went inches from winning it in stoppage time when Teddy Bishop slid in at the far post to meet a low cross but for an excellent interception from Woodman who just about did enough to keep the ball out of the net, as the game went to penalties.
It was a penalty shootout that saw captain Taylor miss City's first attempt before Teddy Bishop saw his penalty saved.
The reliable Pierce Sweeney then struck to score for City, Luke Chambers and Kayden Jackson also scored either side of Tristan Abrahams' thunderous conversion.
Youngster Archie Collins then kept his cool before the shootout turned when Trevor Chalobah missed the target, leaving Lee Martin to seal the win for the Grecians.
Exeter City: Pym, Sweeney, Woodman, A. Martin, Tillson, L. Martin, Stockley (Abrahams, 52), Jay (Collins, 52), Taylor, Brown, Boateng (Sparkes, 61)
Subs not used: Hamon, Forte, Oates, Croll
Ipswich Town: Bialkowski, Donacien (Spence, 45), Knudsen, Chambers, Chalobah, Jackson, Nolan, Ward (Rowe, 77), Sears (Bishop, 65), Nsiala, Edun
Subs not used: Gerken, Skuse, Harrison, Bishop, Rowe, Kenlock
Attendance: 3,675 (Inc, 351, away)