A National Football League final victory against Armagh in 1985 created a momentum that peaked in 1985 when future Monaghan manager Eamonn McEneaney kicked an equalizing point from 48 metres out near the sideline beside the Hogan Stand to draw the All-Ireland semi-final against Kerry on a scoreline of Monaghan 2–09 to Kerry's 1-12.

Paddy Linden saved a penalty, while an Armagh player saw the line barely 30 seconds after coming onto the field as a substitute, following an apparent high tackle on Declan Flanagan.

In the drawn All-Ireland semi-final against Kerry, the absence of David Byrne through injury in the second half probably cost Monaghan victory.

Monaghan's championship run in 1986 consisted of a draw against Down in Castleblayney thanks to a last gap Eamon McEneaney free while in the replay Down emerged victors in Newcastle on a 2–11 to 0–11 score.

Previous wins over Cavan (0-16 to 0-14), again marked by strong performance from Nudie Hughes, and Down (1-11 to 0-09) had brought Monaghan to the Ulster final.

In 1989 Monaghan scraped home with an 0–08 to 0–05 win against Antrim in Casement Park, Belfast, where the homesters literally kicked the game away.

At senior level in 1999, the county U-21 side won the Ulster championship over Donegal thanks to a last-gasp super point from Kieran Tavey.

The team reached the Ulster championship final in 2001 for the first time in 18 years, but they lost 2–13 to 0–13 again to Tyrone, including a late missed penalty when only 4 points separated the sides.

A last-gasp point from Paul Finlay in the final league game against Longford in Clones earned the team a draw and automatic promotion to Division 1 for the first time in 18 years.

This was Monaghan's first visit to Croke Park in 7 years, that resulting in a 1–12 to 0–08 defeat in a National Football League semi-final to Derry back in 1998.

2006 saw Monaghan compete in Division 1A of the National Football League, but after wins to Dublin and a draw with Offaly, the team's season ended in the championship qualifiers with a 0-08 to 0-06 defeat to Wexford.

The game saw continuous rain and wet conditions, and the performance of the referee grabbed headlines on the day[citation needed].

Though the team had a backroom clean-out of trainers and selectors, the introduction of Tyrone native Martin Mc Elkennon to the Oriel set up contributed to a run of seven successive victories in matches: away to Roscommon, home to Longford and Carlow, away to Clare, away trips to London, home to Offaly, away to Leitrim.

Monaghan reached the Dr McKenna Cup semi-final where they lost to Tyrone in Kingspan Breffni Park, Cavan on 13 February 2007.

In the National Football League, Monaghan won all their seven games, including high-scoring first halves against Roscommon, Longford and Carlow.

During the game against Offaly in the penultimate round in Clones, a last-gasp Paul Meegan point in injury time was enough to give Monaghan a 0–13 to 0–12 win, guaranteeing them a semi-final place as table toppers and a position in the revamped Division 2 in 2008.

that Monaghan's full back line and team in general needed a major overhaul prior to the Ulster championship meeting against Down in Newry on 10 June.

Páirc Esler in Newry was the venue for Monaghan's first game of the Ulster championship where they faced a Down team who had disposed of Cavan in the preliminary round after a replay.

Though Paul Finlay was out due to illness, his replacement Rory Woods had a strong performance brought much-needed bulk and skill to trouble Derry's vaunted defence.

A goal by Philip Jordan after 6 minutes put Tyrone in the driving seat, but Monaghan came back to trail by 1–08 to 0–07 at half time.

Monaghan had numerous chances to level the game but settled an injury time point from converted full back Vincent Corey whose switch from No.

Performances by Dessie Mone, Eoin Lennon, Tommy Freeman and man of the match Vincent Corey were chief factors in a 2–12 to 1–07 win which saw the Donegal manager retire afterwards but in August 2007 it appeared as if he may rescind that decision according to newspaper reports.

The game was fixed for 12 August 2007, almost 22 years to the day that Eamon Mc Eneaney scored the equalising point against the same team, now defending all-Ireland champions.

However, a combination of panic and inexperience both on the field and on the line told as Kerry fought back to level terms and go a point in front with a minute left.

Kerry went back home to the south to prepare for a semi-final meeting with Dublin on 26 August which they duly won by 1–15 to 0–16 to qualify for the final against Munster rivals Cork.

The eventual champions were quoted many times in the immediate aftermath that their joust with Monaghan had brought them on in leaps and bounds and steeled them sufficiently for the tests against Dublin and Cork[citation needed].

In addition, manager Seamus Mc Eneaney picked up the Ulster GAA writers personality of the year award.

Monaghan beat Donegal at their own game using the blanket defence system, while Darren Hughes and Conor McManus performed well.

It was tight up until the last 10 minutes when Monaghan added some scores to win, Tommy Freeman coming off the bench and firing over the last point.

This result was coupled with the Minors comeback win earlier in the day defeating Tyrone to complete an historic double.