Former Blues midfielder Lee Martin struck the decisive penalty as Town were beaten 4-2 in a shoot-out by League Two Exeter City following a 1-1 draw to crash out of the Carabao Cup at the first round stage. Kayden Jackson put the Blues ahead in the first half but another ex-Town player Troy Brown equalised in the second to leave the scores level at full-time. Teddy Bishop and Trevoh Chalobah missed their spot-kicks for the Blues before Martin won the tie for the Grecians.
Boss Paul Hurst made three changes with striker Jackson and midfielder Tayo Edun making their full Town debuts, and Freddie Sears returning to the XI.
Cole Skuse and Ellis Harrison dropped to the bench, while Gwion Edwards missed out with a minor quad problem.
Bishop, who last played on Boxing Day, and Danny Rowe were among the subs for the first time this season.
Exeter included two ex-Blues, winger Martin, who was making his full debut for the Grecians, and central defender Brown.
Town started positively and as on Saturday passed the ball around confidently. On six, after good work from Edun, Jonas Knudsen crossed deep from the left but Craig Woodman nodded away ahead of Jon Nolan.
Having struggled to get hold of the ball in the early stages, Exeter began to get on top and in the 15th minute ex-Blue Martin struck a curling effort from 25 yards which Toto Nsiala blocked, although it looked to be going wide in any case.
Town quickly regained the upper hand and on 17 a Knudsen cross was cleared out to Chalobah, whose volley wasn’t too far wide of Grecians’ keeper Christy Pym’s right post.
Chances were rare occurrences but on 26 Janoi Donacien broke into the right of the box and flicked the ball over Pym across the six-yard box but no Town player was on hand to add the final touch and Aaron Martin cleared.
Exeter should have taken the lead on the half hour when Lee Martin was sent away behind the Blues’ backline and crossed to Matt Jay at the far post but the sliding striker somehow scuffed the ball wide when it seemed easier to score.
With eight minutes of the half remaining, Town went in front. Edun skipped past a couple of Exeter players then as he reached halfway sent Jackson away down the left.
The £1.6 million signing from Accrington cut in virtually along the touchline and looked set to cut back to any one of a number of team-mates but instead smashed a shot into the net off Pym at his near post with the keeper covering the cross.
Whether Jackson was shooting or crossing was the subject of debate, however, the 24-year-old appeared to have noticed Pym straying away from his post and had tried something similar from the other flank earlier in the game.
The Blues were a more confident outfit having gone in front and might have doubled their lead just before half-time when a cross ran out to Nolan 12 yards out from where he hit a shot on the turn which was deflected wide off Jake Taylor.
Soon after, the half-time whistle went with the Blues having been in control for the most part, although with Exeter having had the game’s best chance up to Town’s goal through Jay, who really ought to have put his team in front.
As in their previous two games, Town had been more comfortable on the ball than was the case in previous seaosn and played it around slickly at times, with Edun catching the eye, however, without creating too many clear-cut opportunities.
Jordan Spence replaced Donacien ahead of the start of the second half, the right-back presumably having picked up an injury.
The home side went close to an equaliser in the 55th minute when sub Archie Collins broke into the area and hit a shot which deflected into the side-netting off Knudsen. From the corner, Aaron Martin flicked a header wide.
Exeter weren’t too far away again on 59 when Hiram Boateng sent in a dangerous low ball from the left but sub Tristan Abrahams was unable to get a touch at the near post.
Town threatened for the first time since the break in the 62nd minute when Spence sent Jackson away on the right but the goalscorer’s low ball flew behind Edun.
But two minutes later, the Grecians equalised and via one of their former Blues. Jack Sparkes’s low freekick from the right somehow made it into the six-yard box where Bartosz Bialkowski desperately stuck out a toe. However, the keeper was only able to send it straight up in the air and Brown nodded into the net from an inch or so out.
Two minutes after the goal Bishop replaced Sears, then Grecians skipper Jake Taylor was booked for a foul on Nolan.
As the game moved into its final quarter of an hour, Jackson was sent away by Spence and cut the ball back to Nolan, who shot not too far over the bar from the edge of the box. On 78 Rowe took over from Ward.
Edun then shot well over from 20 yards, prior to Blues fitness coach Nathan Winder being shown a yellow card - with coaching staff receiving cautions for the first time this season - for dissent, referee Brett Huxtable having given a freekick to Town when the Blues were still in possession and breaking forward.
Jackson was crowded out as he broke into the area on 81, then Knudsen and Nsiala were both yellow-carded, the Dane for dissent having conceded a freekick and the former Shrewsbury defender for a foul on the edge of the box. From the resultant freekick, Sparkes shot straight at Bialkowski.
Town came close to winning it in the 85th minute when Jackson laid the ball back to Edun, who hit a powerful strike which Pym did well to bat away.
The game was becoming ever more open with penalties looming and two minutes later Abrahams struck a shot across Bialkowski from an angle on the left which the keeper saved low and Chalobah cleared.
In the final minute of scheduled time, Spence appeared to aim a stamp towards Woodman after being rather unnecessarily clattered from behind on the touchline but fortunately appeared not to make contact and little was made of the incident.
Moments after the board was raised signalling four additional minutes, the Blues went close again. Nolan hit a cross-shot from the left and Woodman did well to force the ball out ahead of Bishop inside the six-yard box.
Neither side was able to find a winner in the remaining minutes of an evenly-balanced scrappier second half and the game went to a penalty shoot-out in the traditional format rather than the ABBA system used in the competition last year.
Town got off to the perfect start with Bialkowski saving Taylor’s kick down to his left, but Bishop saw his penalty saved by Pym having hit the ball too close to the Exeter keeper.
Bialkowski almost saved from Pierce Sweeney, pushing his penalty on to the inside of the post but the ball eventually found the net.
Skipper Chambers made it 1-1 with a confidently struck kick, then on-loan Norwich striker Tristan Abrahams put the Grecians back into the lead with a spot-kick into the roof of the net.
Jackson sent Pym the wrong way to make it 2-2 before Collins smashed his penalty home to make it 3-2 to the League Two side.
Chalobah blasted his spot-kick well wide to leave ex-Blue Lee Martin with the chance to put his old club out of the Carabao Cup, which he duly did, beating Bialkowski with a well-struck penalty.
Having just about shaded the first half, Town faded after the break, as they have done in all their games so far this season, and allowed Exeter back into the game with Brown’s goal which was a very poor one to concede from a Blues' perspective.
Another Town cup campaign comes to an early end with the Blues still looking for their first win of the season ahead of Aston Villa’s visit to Portman Road on Saturday and then a similarly tough-looking trip to Derby next Tuesday.
Exeter City: Pym, Sweeney, Brown, A Martin, Woodman, Boateng (Sparkes 62), Tillson, Taylor (c), L Martin, Jay (Collins 52), Stockley (Abrahams 52). Unused: Hamon, Forte, Oates, Croll.
Town: Bialkowski, Donacien (Spence 46), Nsiala, Chambers (c), Knudsen, Chalobah, Edun, Sears (Bishop 66), Nolan, Ward (Rowe 78), Jackson. Unused: Gerken, Skuse, Harrison, Kenlock. Referee: Brett Huxtable (Devon). Att: 3,675 (Town: 351).