The Gills make the long journey back from Carlisle empty-handed after a brace from Ian Harte secures the points at Brunton Park.
Without his inspirational skipper Barry Fuller, sidelined with a broken arm, Mark Stimson restored Chris Palmer to his starting line-up and handed the captain's armband to Danny Jackman
Gillingham started with purpose and should have had the lead as early as the third minute. Dickson's through-ball allowed Simeon Jackson to spring the offside trap, he rounded the keeper, but sliced his finish wide of the near post.
Alan Julian's first taste of the action came after ten minutes had elapsed, Matty Robson testing the Gills custodian with a rising effort from the left of goal which Julian was able to push to safety.
Shortly after, the home side missed a golden opportunity, Harte swinging a free-kick in from the left only to see Dobie's connection blocked by the prone form of Adam Miller, before Gillingham scrambled the ball clear.
After the early promise, the visitors soon found themselves firmly on the back foot as Carlisle pushed and probed down either flank, midfielder Adam Clayton looking particularly influential. Although the Gills could have nicked a goal, against the run of play, as Dennehy's header from Jackman's free-kick came back off the crossbar.
In the 33rd minute a cross from Ian Harte carried to Clayton on the edge of the box, the midfielder steadied himself before firing a low shot goalwards, only to see it drift the wrong side of Julian's left hand upright. Soon after Robson found space to shoot from the left but was denied by a fine block from Garry Richards.
Shortly before half time, Cumbrian's Manager Greg Abbott was sent to the stands after coming on to the field of play to protest Rene Howe's challenge on Ian Harte. Seconds later Carlisle had the lead, as Ian Harte dusted himself down and curled a fine free-kick beyond the dive of Julian and into the top right corner.
The goal rocked Gillingham's confidence and Robson could well have doubled the home side's tally with a stabbed shot from the left that Julian pushed away at full stretch. No doubt the half time whistle was a welcome relief for the Blues.
The second half opened with Dickson winning a corner after a surging run down the right, while Darren Dennehy rescued his defence with a strong challenge to block Duffy's 49th minute half-chance.
Gillingham were dealt a sucker punch on 51 minutes as Chris Palmer was penalised for a reckless challenge on Robson in the box. The midfielder seemed to make a meal of it but referee Tierney pointed to the spot and Harte made no mistake with a ruthless finish.
On 57 minutes it should have been three for Carlisle as Dobie headed across goal for Robson but his finish rolled agonisingly wide of Julian's back post. That sparked a response from Stimson who pulled off Maher, Palmer and Dickson for Oli, Barcham and Stuart Lewis.
An incisive passing move cut the Gills back four to ribbons in the 67th minute as Robson cut back for Dobie, the experienced forward placed a low shot on target but was aggrieved to see Julian fly-hack his effort off the line.
With 20 minutes remaining Rene Howe blazed over from Jackman's corner before Ian Harte missed his hat-trick, curling a stunning 25-yard free-kick just past Julian's left hand post. While moments later Dobie climbed above the Gills back four but headed wide of the mark.
With five minutes of normal time remaining the visitors were almost caught out by a quick counter attack. Dobie racing the length of the field before laying off to Robson who was denied by a good stop from Alan Julian. Keogh also went close to netting a third in time added on, heading Clayton's corner over the bar.
Simeon Jackson's last gasp shot-on-the-turn had Collin scrambling to push it around the post but the resulting corner was wasted, as the Gills winless away league run extends to 17 outings.
Gillingham: Alan Julian, Chris Palmer (Stuart Lewis 62), Garry Richards, Darren Dennehy, John Nutter, Kevin Maher (Dennis Oli 62), Adam Miller, Danny Jackman, Rene Howe, Chris Dickson (Andy Barcham 62), Simeon Jackson
Subs not used: Simon Royce, Josh Gowling, Curtis Weston, James Walker.
Carlisle United: Adam Collin, Evan Horwood, Danny Livesey, Scott Dobie, Matty Robson, Tom Taiwo (Paul Thirlwell 80), Ian Harte, Richard Keogh, Kevan Hurst (Ben Marshall 82), Adam Clayton, Darryl Duffy.
Subs not used: Mark Gillespie, Peter Murphy, Graham Kavanagh, Richard Offiong, Tony Kane