Lee Martin scored a 92nd minute goal as Exeter City provided a shock in the last 16 of the Leasing.com Trophy to knock out League One Ipswich Town at St James Park.
The Grecians took the lead in the match through Nicky Ajose a minute before the break but they were then pegged back by Will Keane's strike before substitute Lee Martin fired in off the post with second remaining to win the match.
City manager Matt Taylor made 10 changes to the Grecians line-up from the side that had beaten Forest Green Rovers in Sky Bet League Two last time out, with only Nigel Atangana keeping his place in the team.
There were welcome first starts, following spells out through injury, for Lewis Ward, Nicky Ajose and Gary Warren, while youngsters Alex Hartridge and Joel Randall returned from their respective loan deals with non-league sides to take a place in the starting XI.
The Grecians started the match well and had the better of the first half chances. Randall, who impressed in the group stage of this competition by netting twice against West Ham under-21s, fired a shot low towards the near corner to force Tomas Holy into an early save.
Then Ajose tried a first-time lobbed finish, from 20 yards out, only to see his effort land on the roof of the net. Jake Taylor then sent a couple of efforts just over the upright before Ipswich managed their first attempt at goal only to see Aristote Nsiala’s header end up in the side netting.
However, as the half wore on, Ipswich began to look more threatening and Keane almost forced an own goal when his shot across the six-yard box ricocheted off the shins of Gary Warren and onto the post.
It was just deserved though, on the balance of the first half play, when City took the lead. Nigel Atangana chipped a ball into the area that found its way to Ajose at the back post and his side-foot finish squirmed between Tomas Holy and his near post to give the Grecians a half-time lead.
The second half started with Ipswich on the front foot, but Jake Taylor put in a superb sliding challenge within a minute of the restart to stop Freddie Sears having a shot at goal from eight yards out and City continued to look threatening every time they broke forward.
On the counter attack created their first chance of the second half moments later as Randall stole the ball back in his own half before racing to the edge of the box and sliding a pass out wide to Ajose, whose cross in was turned behind for a corner at the near post.
On 56 minutes though Ipswich, grabbed an equaliser as Keane raced onto a ball that was flicked on just shot of the area and fired a low finish into the bottom corner. The game could have turned on his head moments later as Teddy Bishop fired towards goal, but Jonny Maxted made a save.
City responded with a free-kick from Matt Jay and then a long range effort from Ajose but neither troubled Holy too much in the Ipswich goal. The next big chance came the visitors’ though with 15 minutes to go as substitute Kayden Jackson latched onto a ball into the box but could only place a right foot shot into the side netting.
Substitute Ryan Bowman got in on the left side of the box and fired a shot towards the near post that Holy saved before the ball looped up in the air and was headed over his own crossbar by James Wilson.
A couple of moments of last ditch defending from Will Dean on the edge of the six-yard box then kept the scores level going into the final 10 minutes of the match. Randall then fizzed in a low cross looking for Bowman before Idris El-Mizouni tested Maxted with shot towards his near post.
Then in injury time it was City who pushed to try and find a winner. However, it looked as though the opportunity had come and gone when Bowman was pulled back by Nsiala on the edge of the box and Jay curled a free-kick towards the top corner that Holy superbly saved.
The Grecians kept the ball alive through, from the corner, and when the ball was crossed back in to the area it bounced kindly for Lee Martin picked up the ball and hit a shot in off the post to put City into the next round.
Exeter City: Maxted, Atangana, Ajose (L Martin, 75), Warren (Dean, 45), Jay, Richardson, Taylor, Randall, Hartridge, Seymour (Bowman, 68), Dyer. Subs not used: Arthur, Collins, Kite, Chrisene
Booked: Jay
Ipswich Town: Holy, Wilson, Edwards, Skuse, Bishop (Idris El-Mizouni, 74), Sears (Jackson, 62), Nsiala, Dozzell, Woolfenden, Kenlock, Keane. Subs not used: Norris, Norwood, Judge, El Mizouni, Garbutt, Dobra.
Booked: Keane, Woolfenden, Nsiali
Attendance: 2,229 (420, away)