Northern Ireland League Cup

The competition began with 32 clubs in a straight knock-out format in February 1987, and included teams from the Irish League B Division until 1997–98. From 1998–99 until 2007–08, only senior (Irish League and Irish Premier League) teams competed, but the competition was opened up to the 17 Championship clubs in 2008–09, and again in 2010–11 to include clubs from Championship 2, after the Championship 2 League Cup was abolished. From 2001–02 until 2007–08, a group stage followed by a knock-out system was used instead of the straight knock-out system, and for two seasons (2008–09 and 2009–10) two-legged home and away aggregate ties were used up until the quarter-finals, instead of single matches.

When it was first introduced in the 1986–87 season, it was one of a number of senior cup competitions run by the Irish League, originally to compensate for the relatively few league fixtures (traditionally 22 or 26), but also as vehicles for sponsorship revenue. The League Cup would have been considered less prestigious than the long-standing Gold Cup and Ulster Cup. Over time however, these other cup competitions were phased out as the number of Irish League fixtures increased and the public appetite for additional competitions reduced, leaving the League Cup as the only cup competition run by the Northern Ireland Football League and now established as the third most prestigious competition in Northern Ireland after the national top-flight and national cup. The actual trophy presented to the winners is the old City Cup, which was another senior Irish League competition that was discontinued in 1975.

The first final took place on 9 May 1987 at Glentoran's ground, the Oval, and was contested by Linfield and Crusaders. Linfield became the inaugural winners of the cup, defeating Crusaders 2–1. Since then, Linfield have been the most successful club in the competition, winning the Cup a record 12 times overall in a record 15 final appearances - their three final defeats all coming against Big Two rivals Glentoran. The most common final has indeed been the Big Two derby, which has occurred seven times - the last of which came in 2005–06. The 1988–89 final, played between the two sides at the Oval on 11 November 1988 was won courtesy of a goal by Glentoran goalkeeper Alan Patterson, via a kick from his own penalty area. This was the first time that a goalkeeper had ever scored in a British football final.

Cliftonville hold the record for the most consecutive wins, having won four successive finals between 2013 and 2016. Fifteen different clubs have reached the final, but only twelve clubs have gone on to win the cup - and only six of those have won the cup more than once. Carrick Rangers (once), along with Larne and Newry City (twice each) are the only three clubs to have played in the final but never won the Cup. Conversely, three clubs have a 100% record in the final, lifting the cup in their sole final appearance to date: Bangor in 1992–93, Lisburn Distillery in 2010–11, and Dungannon Swifts in 2017–18. In 2008–09, Championship side Portadown became the first intermediate club and the first club from outside the top flight to reach the final, and subsequently to win the cup, after defeating Premiership side Newry City 1–0. That was also the first final to be played outside Belfast, with Mourneview Park, Lurgan hosting the match. It was attended by UEFA President Michel Platini and Northern Ireland manager Nigel Worthington who was in Northern Ireland for the FIFA meeting held in Newcastle.

The biggest winning margin ever recorded in a final is 4–0, which has occurred twice: in 1999–2000 when Linfield defeated Coleraine, and in 2012–13 when Cliftonville defeated Crusaders. On four occasions, the same two clubs have met in consecutive finals. Linfield and Glentoran have done so three times: 1997–98 & 1998–99, 2001–02 & 2002–03 and 2004–05 & 2005–06, while Cliftonville and Crusaders repeated the feat in 2012–13 and 2013–14. Both clubs agreed to toss a coin for home advantage in the 2013–14 final, with Cliftonville winning the toss. As a result, Solitude was chosen as the final venue for the first time in the competition's history.

In the 2015–16 competition, Cliftonville became the first club ever to reach four consecutive League Cup finals, and subsequently to win four consecutive Cups, after they defeated Ards 3–0 in the final. Ards were appearing in the final for the third time overall, and became only the second club from outside the top flight ever to reach the League Cup final, emulating Portadown in 2008–09. Ards' previous final appearance had also been against Cliftonville, when they won the Cup 2–0 on penalties after a 0–0 draw in 1994–95. Ards also set a record for the longest gap between final appearances of 21 years between 1994–95 and 2015–16. This broke the previous record of 19 years between Newry City's appearances in 1989–90 and 2008–09.

Following a one-year hiatus in which the cup was not played during the 2020–21 season as a result of the COVID-19 pandemic in Northern Ireland, the competition returned for the 2021–22 season, which saw the final being played on a Sunday for the first time in the competition's history. This attracted a League Cup final record crowd of 11,103 at Windsor Park, where Cliftonville won the cup for the sixth time after a 4–3 win over defending champions Coleraine in extra time. This also became the highest scoring final in the cup's history.