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Gillingham crashed out of the Capital One Cup at Birmingham on Tuesday night.
Championship side Birmingham took a first-half lead through Wes Thomas and the striker doubled the advantage with 18 minutes left.
Gills boss Justin Edinburgh made four changes to his starting XI from the weekend, leaving out some key performers, including five-goal midfielder Bradley Dack.
Central defender Max Ehmer was named in the team for the first time, partnering Adedeji Oshilaja at the back for the second-round match.
Birmingham boss Gary Rowett took the opportunity to look at different players, making nine changes to the side which started their league game against Derby last Friday.
The home side went into the cup contest unbeaten in 10 at St Andrew’s. The Gills had lost their last three games in Birmingham, including a League Cup match in 1997.
Edinburgh’s side, sitting top of League 1 after four games, started the game brightly and had the first decent chance after Koby Arthur lost possession. Ben Williamson managed to make space for a shot but keeper Adam Legzdins turned it wide.
Gillingham were unable to make the most of several set-pieces in the first half, including six corners. As the half wore on the hosts began to see more of the ball and they took the lead on 35 minutes.
A corner of their own was headed down to the waiting Thomas and he swept the ball home from close range past captain-for-the-night Stuart Nelson.
The Gills kept at it and a shot from Williamson was saved by Legzdins before Jake Hessenthaler drove forward and saw his effort deflected wide. For a second successive Tuesday night the Gills were a goal behind at the break.
Thomas went close early in the second half, shooting just wide from outside the area, and Andrew Shinnie also had a go from distance but was well wide.
Williamson put a shot wide for the Gills just before the hour mark and he was withdrawn not long after for last season’s leading scorer Cody McDonald, making his first appearance of the season.
Rory Donnelly came close for the Gills, shooting into the side-netting, but Thomas showed his clinical finishing, firing home after the ball broke for him in the box.
Keeper Nelson was adamant the ball through for the goal from David Davis was offside but the officials ignored the protests.
Birmingham threatened to add to their tally in the final stages. Nicolai Brock-Madsen came close with a header as Gills’ unbeaten start to the season came to an end.
Gillingham: Nelson, Jackson (Egan 74mins), Garmston, Ehmer, Oshilaja, Houghton (Dack 78mins), Hessenthaler, Wright, McGlashan, Williamson (McDonald 62mins), Donnelly. Subs: G Morris, Norris, Dickenson, Oldaker.
Birmingham: Legzdins, Eardley, Robinson, Kieftenbeld, Thomas (Brock-Madsen 77mins), Hancox, Maghoma, Shinnie (Brown 83mins), Spector, Arthur (Soloman 77mins), Davis. Subs: Kuszczak, Gray, Donaldson, Morrison.
Attendance: 9,275 (382 away)