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Tranmere 4 Gillingham 2
Gillingham twice came from behind but eventually left Prenton Park empty-handed in League 1 on Saturday.
Goals from Curtis Weston and Adam Miller dragged the Gills level in either half but they were eventually beaten by substitute Terry Gornell's 20-yard drive after 72 minutes and a late goal from Ian Thomas-Moore.
The Gills trailed as early as the fifth minute when Shaleum Logan’s right-wing cross was met by home skipper Thomas-Moore to head beyond keeper Alan Julian.
But they were level 11 minutes before the break when Mark Bentley's header down found Simeon Jackson and he laid the ball back for Weston. Making room for himself, the Gills midfielder hit fly from 25 yards and left keeper Luke Daniels rooted to the spot with a low drive into the far corner.
Mark Stimson found his team behind just three minutes into the second half when John Welsh collected Logan's throw-in and volleyed home from 25 yards.
However, the Gills quickly levelled when Adam Miller set up Andy Barcham, who turned inside Logan before curling home from the edge of the penalty area after 53 minutes.
Gillingham wasted a number of good openings in the second half and they were made to pay the price after 72 minutes. Substitute Gornell had only been on for two minutes but he latched on to a loose ball on the edge of the box and fired home.
Mark McCammon and Chris Palmer were introduced late on but the Gills were unable to hit back for a third time and ended up conceding a fourth in stoppage time when Thomas-More headed in unmarked from close range.
Stimson said: "We have to make sure we don't give people easy goals if we're going to achieve something this year.
"We conceded some sloppy goals. They got the ball into our box too easily for the first goal - and for the second goal we let one of their players make a run on us.
"When it was 2-2 we looked like we would go on and win but players decided not to shoot when they were in great positions.
"I'm disappointed but I didn't think we deserved to lose 4-2. We played some really good stuff in spells and you wouldn't have thought we were the away team."
Gillingham: Julian, Fuller, Nutter, Richards, Gowling, Bentley (McCammon 81), Miller, Weston, Payne (Palmer 81), Barcham, Jackson. Subs not used: Royce, Maher, Yussuff, Rooney, Erskine.
Tranmere: Daniels, Logan, Cresswell, Goodison, Gunning, McLaren, Mahon (Edds 77), Welsh, Shuker, Moore, Curran (Gornell 70). Subs not used: Collister, Taylor, Barnett, Fraughan, Macauley.
Attendance: 5,590.