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Three of the four also being long distance trips to then Premiership outfit Charlton in 2006-07 and Bristol City this season, while the other of those was a journey to London to play Queens Park Rangers in 2008-09. The only home second round tie earned being an uninspiring tie against Coventry City.
United have met the Robins once before in the League Cup at Ashton Gate, that again in the second round of 1981-82 back in the days when it took two legs to decide a tie. Carlisle, having drawn 0-0 at Brunton Park in the opening game, losing 2-1 in the return leg in Bristol despite having been 1-0 up at half-time thanks to a Gordon Staniforth penalty.
The two sides have also met in the competition in a, yep - second round tie, one other time, that being a hearty 4-1 win at Brunton Park for Carlisle in late 1964 thanks to goals from Hughie McIlmoyle (2), Barry Brayton and Johnny Evans. That match only remarkably being 11 years older than the last time United made it to round three when they lost 2-0 at Everton in the 1975-76 campaign.
Carlisle's overall record at Ashton Gate is pretty grim over the years too, the Blues only claiming two wins and five draws from the 19 games played in south Bristol. Perhaps the only two United players looking forward to the 550 mile round trip being former City men Joe Anyinsah (2 starts and 7 substitute appearances) and the injured Richard Keogh (30 starts and 24 substitute appearances).
Our best effort in the competition of course came in 1969/70 as a second division outfit when wins over Huddersfield, Blackburn, Chelsea and Oxford (in a replay) set up a two-legged semi-final clash against a West Bromwich side managed by Alan Ashman and featuring Dennis Martin on the wing. Bob Stokoe meanwhile the Blues boss responsible for guiding United to their first ever final four game in a major domestic trophy, that factor no doubt having a part to play in an attendance of 20,322 at Brunton Park in the first leg.
Nerves for either side didn't help the quality of the game though and it was the visitors who were perhaps on top in the first half. Carlisle goalkeeper Allan Ross doing more work than his opposite number John Osborne, although Bob Hatton did have a header that scraped the top of the Albion crossbar. United however got on top after the break and, but for Osborne, could have scored more goals than the solitary one they did get to take to the Hawthorns through Frank Barton.
In the second leg, in front of 32,791 spectators, the Cumbrians found themselves just 45 minutes away from Wembley on the back of a 0-0 half-time scoreline. Carlisle though, after Bob Hatton had hit the inside of the post shortly after the break, eventually collapsing to a 4-1 defeat. Barton scoring once more for the Cumbrians while Bobby Hope, Tony Brown, Colin Suggett and future United man Martin all found the back of Allan Ross's net to break Carlisle hearts.
Since the glory days of the mid-70s though the League Cup has not been kind to United at all, the Blues failing to reach even the third round since 1975/76, the club in that season eventually losing 2-0 at Everton. Our best effort prior to the semi-final against West Brom being a 2-1 quarter-final defeat away to Queens Park Rangers in 1966/67, a season in which we finished an excellent third in the old Division Two behind Coventry City and Wolverhampton Wanderers.
Should Carlisle win tonight's tie then the third round draw of the Carling Cup will take place at around 12.15pm on Saturday 29th August, live on Sky Sports programme 'Soccer Saturday'. The remaining seven Premier League teams who are in European competition, in Arsenal, Aston Villa, Chelsea, Everton, Fulham, Liverpool and Manchester United all come into the draw at this stage.