Keeper Woody Williamson was the shootout hero as a ten-man Town XI beat hosts Stowmarket Town 4-3 on penalties after a goalless draw in Tuesday's Suffolk FA Premier Cup first-round match.
The Blues, who conceded home advantage, usually field an U18s side in this competition, but it was much more of an U21s team that took to the field at Greens Meadow with John McGreal and David Wright in charge.
Both sides had a sighter of goal inside the opening ten minutes with Harley Jordan-Smith firing a low free-kick just wide for the home side early on, before Chuks Uzor-Greey turned on the edge of the Stow box but his effort was similarly wide of the target.
Scotland U19 international Williamson, who is currently on loan with Chelmsford City, made a good block at his near post to deny Brandon Salisbury, who had been released on the hosts' right side, and then Olly Davis curled a low effort just wide at the other end.
Davis thought he'd opened the scoring midway through the first half when he ran onto a through ball and finished well into the far bottom corner, only to see the assistant referee's flag raised for offside.
Town had generally been comfortable in possession without creating any clear-cut chances but they were nearly caught out five minutes before the break when Salisbury intercepted a loose pass out from the back and played a one-two with Josh Buckles, but the former dragged his shot wide of the near post from a good position.
However, there was still time for the young Blues to come even closer when Jesse Nwabueze - who spent a short spell on loan at Stowmarket in 2021/22 - latched onto a long kick from Williamson. The attacker cut in from the left and curled a right-foot shot that cannoned off the far post.
The Thurlow Nunn Premier Division side made a good start to the second half and a short corner routine eventually led to Ben Smith seeing his effort from the edge of the box deflect just wide.
On 50, Town centre-back Callum Frith picked up the game's first caution for what looked a fairly innocuous foul on the halfway line, before Uzor-Greey was replaced after picking up a knock.
Jordan-Smith burst through moments later but his shot from a slight angle was straight at Williamson, before home stopper Charlie De Larabell gathered a stinging effort from Nwabueze at the second attempt.
Aiden Phair was then gifted the ball on the edge of the Town box but Williamson again did well to get down and keep the ball out, with the rebound being hacked clear just in time.
On 76 the dangerous Salisbury ran onto a long kick from De Larabell and found himself through on goal, but his effort clipped the outside of the near post.
Stowmarket were looking the more likely team to get a winning goal and Williamson made a fine save to deny Jordan-Smith by pushing his dipping volley away from danger.
Lively sub Ashton Boswell then teed up Rio Morgan at the other end but the Northern Ireland U19 international blazed well over from the edge of the box.
With three minutes of normal time remaining, Frith was shown his second yellow card and a subsequent red after hauling down Buckles after the home striker turned to run onto a ball in behind the Town backline.
The only chance in stoppage time fell to Town but Nwabueze saw his free-kick from the edge of the box deflect off the top of the wall, and De Larabell did well to adjust and tip the ball over the bar.
With neither side able to find the net, the tie moved straight to penalties with Luke Towler opening the scoring for Town and Salisbury then levelling for the home side.
Leon Elliott saw his spot-kick saved by De Larabell, with Will Wharton-Richardson putting Stow ahead. Nwabueze, Smith and Boswell scored the next three penalties but De Larabell lifted his high over the bar.
Morgan slotted Town's fifth penalty home and then Williamson made a good stop to deny Jordan-Smith and send Town through to the second round where they will again concede home advantage, and travel to Cornard United.
Overall, it was a fairly disappointing display from Town, who ultimately seemed to run out of ideas on how to break a resolute Stowmarket defence down.
Town's U21s are in action at Needham Market on Thursday evening when they host Everton (KO 7pm) in the second of their Premier League Cup group games.
Town XI: Williamson, Elliott, Jambang, Frith, Curtis, Onuchukwu, Davis (Boswell 64), Towler, Uzor (Mauge 53), Morgan, Nwabueze. Unused: Chenery, Fleischer, Compton. Att: 242.