The competition was launched with Setanta providing support for prize money (€350,000) and sponsorship (€1.6 million over four years).

In June 2009, the company went into administration and ceased broadcasting in Great Britain, putting the future of the competition in doubt.

The quarter-final winners again played a two-legged knockout tie in the semi-finals for a place in the final, which was a single game.

However, both clubs declined the invitation to take part, citing match scheduling and reduced prize money as their reasons for deciding not to enter.

The eventual winners of the Cup, Linfield, started the campaign poorly losing 2–1 to Longford before going on to win their remaining group matches and beating pre-tournament favourites Shelbourne.

The top two teams in each group entered a semi-final round with the winner progressing to the final.

On 30 January 2007 however, Shelbourne announced that they were withdrawing from the competition for reasons relating to their financial troubles and the fact that they would be unlikely to field a team of players.

This meant that Drogheda had to travel away from home to meet the winners of Group 2, who were St. Patrick's Athletic.

Meanwhile, Cork City, who finished second in Group 2 had to travel to Windsor Park to play Linfield.

Drogheda claimed the trophy for a second consecutive year thanks to two penalty saves from Mikko Vilmunen.

The draw for the 2008 competition was made on 17 January 2008, having been postponed since December 2007 to allow time for an agreement to be reached over the League of Ireland fixtures for 2008.

As Derry City beat Cobh Ramblers 2–1 in the play-off on 19 November 2007, they claimed the remaining spot.

The competition commenced on 14 February 2011, and ended with the final on 14 May 2011, which was played at the Tallaght Stadium, Dublin and was won by Shamrock Rovers.

Milo Corcoran, Chairman of the Setanta Sports Cup Organising Committee said he believed the knock-out format would "add even greater excitement to the tournament".

The final was played at the Oval, Belfast and was won by Crusaders for the first time, defeating Derry City 5–4 on penalties after a 2–2 draw.

Cup holders Crusaders, 2012 FAI Cup winners Derry City, 2011–12 IFA Premiership champions Linfield and 2012 League of Ireland champions Sligo Rovers entered the competition in the quarter-finals, with the remaining eight clubs entering in the first round.

The final was played at the Tallaght Stadium, Dublin and was won by Shamrock Rovers for the second time.

However, in December 2013 both clubs declined the invitation to take part, citing match scheduling and reduced prize money as their reasons for deciding not to enter.

However, in May 2015, Northern Ireland Football League clubs initially voiced concerns over fixture scheduling – particularly plans for midweek games – raising doubts as to the competition's viability.