The Hatters exited the Carabao Cup at the third round stage as League One side Exeter City caused an upset at St James Park with Deme Mitchell's late strike proving the difference between the two sides.
With ten changes from the side that drew with Wolves on Saturday, including a first senior start for Joe Johnson, Town moved the ball well in the early stages with the 17-year-old on the left of a back three alongside Mads Andersen and debutant Teden Mengi.
The game’s first opportunities came the Hatters’ way after Mengi had endeared himself to the travelling fans with a perfectly timed tackle on flying Exeter winger Vince Harper as the hosts looked to break.
Luke Berry fired the first warning shot on eight minutes, Grecians keeper Vil Sinsalo tipping his 20-yarder over his bar, before Cauley Woodrow rattled the outside of the post after ghosting into the box direct from an Alfie Doughty throw three minutes later.
Exeter’s response was positive, James Scott collecting the ball halfway inside the Town half and whistling a shot just past Tim Krul’s right post, before Mitchell cut in from the right flank and tested the Dutchman at his near post.
Town were always a threat, however, Andersen heading a Doughty free-kick narrowly wide just before the half-hour, Berry and Elijah Adebayo seeing quickfire volleys blocked in a goalmouth scramble from a Ryan Giles corner soon after.
Exeter midfielder Caleb Watts skied an effort that threatened only a bay window in the houses behind the Town fans in the St James Road Stand, before Mengi became the first player into referee James Bell’s book for a challenge on Harper that was nowhere near as well-timed as his first.
He was soon joined by Chong for a shove on the Exeter wideman in full flight, before Kyle Taylor kept his effort slightly lower than Watts and Pelly Ruddock Mpanzu at the other end, after capitalising on some loose defending from City captain Will Aimson.
Goalless at the break, Exeter came quickly out of the blocks as they attacked towards their own fans on the Big Bank, Mitchell trying his luck from distance after a loose back-pass from Giles presented them with an early corner.
Krul was called into action again on the hour as Mitchell raced down the right and the keeper’s outstretched leg, Taylor missing the target with the rebound from close range.
Edwards made a quadruple substitution, replacing Johnson, Doughty, Chong and Woodrow with Amari’i Bell, Issa Kabore, Chiedozie Ogbene and Jacob Brown.
Town started to enjoy more possession and Adebayo’s stooping header from a Giles cross flew just wide, before a raking pass from Mengi put the former Wolves man in on the left again, Brown meeting this perfectly delivered centre with a header straight at Sinsalo.
The fifth change came with 15 minutes left, Edwards introducing Carlton Morris for Adebayo and the top scorer was next to head a Giles delivery at goal, his effort cleared off the line before another pinpoint Giles cross found Brown once again, this time the Scotland forward’s glancing header flying past the far post.
Just when the Town were threatening as the close stages neared, the hosts had their breakthrough with seven minutes of normal time remaining when Yanic Wildschut’s deep cross from the right found its way to Mitchell at the far post, via a loose touch by Kabore, and the City forward rifled into the roof of the Town net.
As the Hatters pushed for an equaliser to force penalties, Mitchell intercepted a Berry pass on the edge of his box and carried the ball towards the Town area, although his attempted chip over Krul was too high.
The Exeter goalscorer’s night was over in the 88th minute, however, when a foul on Kabore earned him a second yellow card, and the announcement of another seven minutes of added time gave the Hatters hope.
For all the territory and possession, they failed to create another clear-cut chance however, and the travelling faithful set off on the long journey home disappointed, but still having given their team their usual warm reception as they thanked them for their brilliant midweek support.
Now it's onto Everton and the search for Premier League points. See you then.
Town: Krul; Doughty (sub Kabore 64), Mengi, Andersen, Johnson (sub Bell 64), Giles; Mpanzu, Chong (sub Brown 64), Berry; Woodrow (sub Ogbene 64), Adebayo (sub Morris 75).
Subs not used: Shea, Burke, Burger, Luker.
Attendance: 7,360 including 708 backing the Town.