Despite the visitors coming off the back of a 6-0 Championship defeat away to Blackpool at the weekend they started brightly and Massimo Luongo went close early on with a curling effort that just zipped past the United woodwork. Jay Emmanuel-Thomas then the next Town man on the attack only for him to see his shot well blocked by Carlisle centre-half Peter Murphy, with Adam Collin then shortly afterwards having to make a smart stop from Josh Carson's close range shot following a low cross in from Lee Martin.
The United goalkeeper was powerless to stop Ipswich taking the lead in the 23rd minute though when Emmanuel-Thomas fed possession into Luongo for a neat 18-yard finish low into the bottom corner of the Carlisle net. The home side came back into it however and first Liam Noble shot wide before Danny Cadamarteri headed off target from a Matt Robson cross. Robson then having two pot-shots from distance dealt with relatively comfortably by Town stopper Scott Loach.
The turning point in the game then came on 37 minutes when Michael Chopra was through one-on-one with Collin only to see his pretty weak effort on goal saved away to Collin's right, that stopping the Tractor Boys from taking what may have been an unassailabe 2-0 lead.The last action of the opening period seeing Paul Thirlwell for United and then Chopra for the visitors firing drives from distance high over the respective away and home crossbars.
Into the second-half and Mike Edwards had a header held by Loach as Carlisle pressed, with James Berrett shooting narrowly wide and then Robson cracking an effort over the top as United began to take control of the game. It wasn't all one way traffic though as Paddy Madden has to clear off the line to prevent a Murphy own goal from an Ipswich corner, with Madden though proving wasteful at the other end as he sent two unmarked headers from Robson crosses in well over the top.
Robson then deciding to take matters into his own hands only to have his shot blocked by Andy Drury, with Town's Jason Scotland moments later toe-poking an effort into the United side-netting from a tight angle. It was Carlisle's substitute who proved to be the hero as, after first lashing a half-volley on goal inches wide Mark Beck was able to head a Robson cross in from the left in stoppage time powerfully into the back of the Town net to take us into a further 30 minutes to decide matters.
The first chance again falling to Madden who once more could only head over the top from a Robson cross before Beck and Dave Symington produced a lovely one-two on 99 minutes which saw Symington charge goalwards before hammering a shot across Loach and into the far corner of the net to make it 2-1 to Carlisle. Symington in the remaining 21 minutes then the only player to really put in a testing effort as Loach had to scramble to save his powerful 28-yard drive as United saw the rest of extra-time out with ease to make it into round three of the Capital One Cup.