The Gills kicked off their Checkatrade.com Trophy campaign on Tuesday evening with a defeat at home against Luton Town.
Luton Town took the lead in the 10th minute through Frankie Musonda, and they then extended that lead before the half hour mark through Jonathan Smith.
The Gills did find a way back into the game, but they had to wait until almost the full time whistle when Darren Oldaker scored his first goal for the club.
Manager Justin Edinburgh made six changes from the team that won away in the league at Shrewsbury Town on Saturday afternoon.
Stuart Nelson returned in goal, while Darren Oldaker, Elliott List, Jake Hessenthaler, Mitchell Dickenson and Bradley Dack all coming into the line-up.
The visitors were in front within ten minutes of kick-off when List was penalised for a foul. The resulting free kick saw some confusion in the Gills back four, as they all stopped expecting Nelson to come out and collect the ball. He didn’t and Musanda headed home.
Having changed their entire starting eleven, the visitors didn’t look to be as inexperienced as their line-up was as they were impressive in their first half.
The Luton keeper making his debut was called into action, when he had to get down low to save a Jay Emmanuel-Thomas effort from the Gills only real effort of the first half, as the Gills striker had used his strength to power his way into the area.
Luton spurred on, doubled their advantage shortly before the half hour mark, when Jake Gray did well to pull the ball back into the area, picking out teammate Smith via at least one deflection, who slotted home his effort.
The League Two side were certainly in the ascendency as the half time whistle approached and could have been further ahead, only for Nelson to push the effort away.
As the second half kicked off it looked as though it was likely to be more of the same from the visitors as once again Vassell saw an effort saved by Nelson.
At half time however Edinburgh had made a double substitution in an effort to try and get the Gills back in the game, with O’Hara replacing Dack and Donnelly replacing Emmanuel-Thomas.
It was Oldaker who would have the first chance for the home side in the 52nd minute when he fired a shot goalwards from 18 yards out, but King was equal to the shot.
McDonald was the next to go close, as the clock hit the hour mark, List showed some great pace down the wing before feeding O’Hara. The former Spurs man then picked out McDonald out, but once again King was quick to react and smother the shot.
On 70 minutes it was hard to see how Luton didn’t wrap the game up, Vassell raced into the area and then crossed to the back post, where Josh McQuoid managed to send his header into the Brian Moore Stand, when it looked easier to score.
Oldaker then got a goal back for the Gills in injury time, and it was nothing short of what the youngster deserved for his performance. He fired into the net from just outside the area to salvage some pride for the Gills.
The Gills are back in action on Sunday afternoon live on Sky Sports when Sheffield United visit the Priestfield Stadium.
Full time 1-2
Gills: Nelson, Osadebe, List, Pask, Dickenson (Stevenson, 62), Ehmer, Hessenthaler, Oldaker, Dack (O’Hara, 46), Emmanuel-Thomas (Donnelly, 46), McDonald.
Subs not used: Bond, Oshilaja, Cundle, Wright.
Luton Town: King, Smith, Gray, Banton (Tomlinson, 90), Vassell, McQuoid (Atkinson, 85), Bakinson, Cotter, Justin, Musonda, Famewo.
Subs not used: Snelus, Hinds, Bean, Read, Gooch.
Att 2,128 (137 away)