Leitrim's football history has brought sparse reward. They first competed in the All-Ireland in the 1907 championship. They were beaten by Roscommon on a score of 0-03 to 0-01 in the Connacht semi-final in their first ever match. The county won its first ever match in the 1910 championship, beating Sligo in the Connacht quarter-final by 0-03 to 0-00. They were then beaten by Galway in the semi-final.
Leitrim did not record another win until the 1914 championship. They beat Sligo by 5-07 0-02 to qualify for their first ever Connacht final but were beaten by Roscommon in the decider. In the semi-final of the 1924 Connacht Championship, Leitrim forced Mayo to a draw, then refused to play extra-time. Galway went on to be beaten in the final by Mayo following a replay. In 1927, with training from Sean O'Hehir, father of the veteran radio commentator Micheál and with the help of good fortune when Connacht semi-finalists Roscommon had to line out without five players whose car had broken down, Leitrim won their first ever Connacht title. Leitrim won the Connacht title and held Kerry to two points in the semi-final of the All-Ireland Senior Football Championship.
In the days of Cathal Flynn and Packie McGarty, both Connacht Railway Cup players, Leitrim lost four successive Connacht finals to Galway between 1957 and 1960, coming closest in 1958 when they equalised midway through the second half but were defeated by two points (Cathal Flynn scored 1-6). Flynn retired in 1966 from inter-county football while McGarty was at the end of his career when Leitrim were heavily beaten by a score 4-15 to 0-7 against Mayo in the Connacht final in 1967, scoring only one point from play. Leitrim won the National Football League Division 2 title and contested the 1959 NFL semi-final with a changed fullback line but were beaten by Derry by seven points. A new generation of Leitrim under-21 players hosted and nearly beat the great Kerry team at Carrick-on-Shannon in 1977 before losing by five points, 3-13 to 3-8. The expected breakthrough from Michael Martin and his men never happened.
John O'Mahony was apppointed Leitrim manager to build on the success of the Under-21 team that won the 1991 Connacht Championship. He managed to take Leitrim to the final of the 1994 Connacht Championship. Leitrim did not have an easy route to the final, beating Roscommon by a point and only overcoming Galway by a point in a replay. They took on Mayo in the final, overcoming O'Mahony's native county by two points in Hyde Park. O'Mahony's feat in leading the team that is traditionally the weakest in the province to that title is still heralded nationally to this day. Leitrim were ultimately beaten in the All-Ireland semi-final by Dublin at Croke Park. Since losing to Sligo in 1989, Leitrim had suffered a series of near-misses, and might have followed up 1994 against Galway, losing by a single point in 1995 and two points in 1996. The first county to benefit under the parentage rule was also the first to lose their big catch, with the loss of Declan Darcy to the Dublin depleting the panel in 1998, bringing Leitrim's most successful era to an end.
Leitrim sprung a massive shock when they managed to win the FBD Insurance League in 2013, defeating their southern neighbours Sligo in the final. This was the county's fourth ever trophy and their first since 1994. As the Irish Independent reported, "There may have been no danger of any cows going unmilked in Leitrim after this game, but winning their first FBD League title – and their first trophy in 19 years – sparked off some understandable early season celebrations for Connacht's traditional minnows". They managed to retain the title in 2014, defeating Roscommon in the final.
^Breheny, Martin (24 November 2012). "The import and export business". Irish Independent (Independent News & Media). Retrieved 24 November 2012. "the highest 'outside' football achiever in terms of titles is John O'Mahony...Steering Galway to All-Ireland wins in 1998 and 2001, ending a barren spell that extended back to 1966, was a huge achievement for O'Mahony, but, in many ways, leading Leitrim to their first Connacht title for 67 years in 1994 was just as noteworthy...given the small base from which Leitrim operate, winning a Connacht title is always a massive success story. All the more so in 1994 when they had to beat Galway, Roscommon and Mayo to claim the title."