It was a trip into south east London for the Blues on Friday night as they came up against National League south side Dulwich Hamlet at Champion Hill.
Some 44 places separated the teams heading into the kick off and the TV cameras were out in force, with the game being shown live on BBC2 and in front of a sold-out stadium.
Defender Byron Webster stepped back into the fold, having served his one-match suspension, and that meant Mo Sagaf dropped to the bench as manager Steven Pressley went with a 3-4-3 formation.
The away side had an early cross from Chapman to contend with when the livewire found space on the right. Collin was off his line quickly to punch it away.
Carlisle went close at the other end when Thomas showed good skill as he twisted and turned his way past Nathan Smith. The cross was flicked on at the near post, then put back into the mix by Iredale. Olomola spun on it and his volley was going in until it was stopped on the line. A scramble followed but the referee's whistle blew to calm things down.
It was a frenetic pace to the game and Webster came under pressure when Yusuff stepped in to stop him from making a clearance. The striker suddenly had room and his fierce effort smashed into Branthwaite before heading into the side of the net.
The Cumbrians broke from the corner and McKirdy had acres of space as he ran with the ball from the halfway line. He beat the defender then popped the ball into the box, and Olufela Olomola said thank you very much as he volleyed it into the waiting net.
United were almost architects of their own downfall when Bridge was tackled inside his own box as he tried to take it out of the danger area. Monakana was suddenly through but Mellish threw a leg out to make the block.
Dulwich stayed on the attack and Nathan Smith was disappointed with himself when he put a 25-yard free kick high over the bar. Another set piece for the home side, this time from Vose, had to be cleared at the front post when it was swung in from the right hand touchline. The follow up shot from Christian Smith bobbled past the upright.
The hosts continued to probe, with both wide men constantly asking for the ball, and the away side's struggle to keep possession also invited unwanted pressure.
And Marvin McCoy was the width of the woodwork away from bringing things level on 27 minutes when he was given plenty of grass to work with. He dropped a shoulder as he came up against Iredale and his whipped and rasping shot skimmed the top of the bar on its way over the target.
United had to work hard to keep their opponents at bay, with purple shirts pressing whenever they lost the ball, but a quick break down the right wing from the Blues saw Gethin Jones go on a sprint when he took a touch from a short pass from Bridge. The low near post cross was met by Harry McKirdy and a cheeky back heel at the front stick left Grainger with no chance.
Carlisle survived a scare before the break when Monakana ran towards the 18-yard box. He dropped a shoulder and let fly but it hit a defender and spun away to safety.
And there was another sigh of relief when an sinswinging delivery from Chapman was headed by Branthwaite as he tried to send it away. He wasn't too sure where it was going and was mightily relieved to see it bulge the side netting.
United fashioned the first chance after the break when Jones was fouled 25-yards out, just after the Cumbrians had broken at pace from a corner via quick thinking from Olomola. Thomas beat the wall but it curled into Grainger's hands.
Dulwich were right back in it on 49 minutes when Monakana flighted a beauty of a free kick into the box from the right wing. Christian Smith jumped highest and he left Collin rooted to the spot as he guided his header into the bottom corner.
The home team thought they were back on terms moments later when Chapman drilled a 28-yard free kick over the wall. The keeper could only watch as it edged past his post.
But the two-goal advantage was restored when Mike Jones scored an absolute beauty from distance when Olomola spotted him in an unmarked position. It was going in from the moment it left his boot.
And the midfielder tried to repeat the feat when his team mates worked the ball his way with plenty in support. He needed a touch but it was just a yard over the angle of post and bar as it started to rise high.
A Bridge free kick then caused all kinds of chaos as Branthwaite volleyed it low. It came to Webster but he had to readjust and he could only toe poke it wide.
Superb skill from McKirdy took him away from some tight marking as the visitors started to edge on top, but an excellent fingertip save from Grainger prevented a goal as his touch took it behind for a corner.
McKirdy shot wide from close range following a run from Bridge, with the Hamlet seeing less of the ball in the visiting half, but susbtitute Dipo Akinyemi nearly wrote his name in lights when he nipped in to get onto a dipping pass from Chapman. He couldn't quite find the angle to test Adam Collin.
The Carlisle stopper was on hand to make a comfortable save when Chapman tried one from long range, and he was in the right place again when a deep free kick was nicked goalwards by Orlu.
A second wind came for the Hamlet with 10 minutes left to play, as they once again pushed forward, but Clunis was wayward with a shot on the run which sailed out of the stadium.
Progression was sealed for the Cumbrians with five minutes left to play when Mo Sagaf played an inch perfect through ball for McKirdy to chase. He kept his cool to slot the ball home for his second of the evening, and to see off the challenge of a very competent and hard-working Dulwich Hamlet outfit.
There was still time for Mills to drag one wide from 10-yards for the home team in time added on, but it was the 500 travelling supporters who were able to celebrate come the final whistle.
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Goals
Dulwich Hamlet - C Smith (49)
Carlisle United - Olomola (8), McKirdy (37 & 86), M Jones (55)
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Bookings
Dulwich Hamlet - C Smith (41)
Carlisle United - Webster (52), Loft (82)
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Teams
Dulwich Hamlet - Grainger (gk), McCoy, N Smith, Dempsey, Orlu (Hunte 85), C Smith, Chapman, Vose, Mills (c), Yusuff (Akinyemi 67), Monakana (Clunis 67). Subs - Edwards (gk), Connors, Ijaha, Taylor.
Carlisle United - Collin (gk), (c), Branthwaite, Webster, Mellish, G Jones, Bridge (Carroll 85), M Jones, Iredale, McKirdy, Thomas (Sagaf 57), Olomola (Loft 80). Subs - Gray, Hope, Knight-Percival, Sorensen.
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Match officials
Referee - James Oldham
Assistant Referee - Andrew Aylott
Assistant Referee - Paul Lister
Fourth Official - Charles Breakspear
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Attendance - 3,301 (500 away fans)