Doncaster Rovers 1-1 Manchester City (3-0 pens) - Round 2 - 2005/06
The score was 0-0 in this Second Round clash and with no replay the tie went to extra-time. City took the lead before Rovers equalised through a Michael McIndoe penalty to force the shoot-out.
McIndoe, James Coppinger and Paul Heffernan all scored their spot-kicks for Rovers, but Darius Vassell hit the bar and Antoine Sibierski and Richard Dunne saw their penalties saved by substitute goalkeeper Jan Budtz, who had only come on after an injury to Andy Warrington.
Chester City 3-3 Bolton Wanderers (2-0) – Round 1 – 1983/84
Back in the days of two-legged ties in the early rounds of the League Cup, Bolton were 3-0 winners in the North West in the first instalment against Chester City.
Then, the following month, Chester won their home leg by the same scoreline, meaning the game went to spot-kicks, where the home side triumphed 2-0 to advance into the Second Round.
Mansfield Town 1-1 Stoke City (3-0 pens) - Round 1 – 2005/06
Again, with no replay in this First Round clash in the 2005/06 season, penalties would separate Mansfield and Stoke for a place in Round 2. Richard Barker, Rhys Day and Gareth Jelleyman all converted for the Stags, while Jason White saved from Carl Hoefkens before David Brammer and Michael Duberry missed for the Potters.
Leicester City 3-3 Fulham (3-0 pens) – Quarter-Final - 1999/00
Leicester twice came from behind having been 2-0 and 3-2 down against Fulham, but forced penalties after 120 minutes in this last-eight tie. The Cottagers failed to convert from 12 yards three times, but the Foxes were clinical with all of their spot-kicks. Leicester, who had overcome Leeds United on penalties in the previous round, went onto the Final where they beat Tranmere Rovers 2-1 at Wembley.
Millwall 3-3 Northampton Town (2-0 pens) - Round 1 – 1997/98
Having delved through the League Cup annals, this gem has been proven as statistically the worst penalty shoot-out in the competition’s 54-year history with two scored and seven missed – a 22% conversion rate.
Also in the days of two-legged ties in the early rounds, Northampton won 2-1 at Sixfields before Millwall matched that in the second instalment to initiate extra-time then penalties.
The Lions were successful with their first attempt, but remarkably seven successive efforts were then missed. Millwall then scored their second with the ninth of the night, to wrap up the evening’s entertainment and progress into Round 2.