1986

The Annual General Meeting was held in Creggan Community Centre on Sunday 17th November 1985. A remarkable feature was that the Committee was returned in block for a further year with the exception of Brian Hollywood and John Conway who did not want to carry on. Ed Fox from Creggan was willing to train the team as he had taken over after Benny Haughey went to the USA in 1985. Peter Tracey and Sean Clarke were nominated as selectors if they were required.

Much discussion now centred on the Club Development, as well as playing activities. One of the big decisions taken was to proceed with plans to build dressing rooms and fence the new field.

The league performances of the team were similar to the previous year, with a record as follows: played 17, won 9, draw 1, lost 7, pts 19. However in the Championship, progress was made. The first round hurdle was crossed for the first time since 1979 when Castlederg were defeated by 0-07 to 1-3. In the second round, Galbally provided the opposition. After a wait of five weeks due to Tyrone's appearance in the All-Ireland Final, the game was finally played following the Senior Final at Pomeroy. An under strength Greencastle team led until the last kick of the game, when Galbally equalised from a free. The score finished 5 points each. The replay a week later resulted in a victory for Galbally by 1-16 to 2-04.

1987

The Annual General Meeting was again held in Creggan Community Centre on 23rd November 1986. For the third year running, the same Committee was elected and this must have created some sort of record.

The record on the playing field was very similar to the previous year. In the league the club occupied a mid-table position with a record of played 17, won 7, draw 3, lost 7, pts 17. In the Frank O'Neill Cup, the usual good showing was put up. Moortown fell in the first round in McLaughlin's Holm and another senior team, Omagh put paid to Greencastle with a narrow victory.

The Annual Championship campaign got underway with a first round clash with Derrytresk at Cookstown. After probably the best Junior Championship game of the season, Greencastle triumphed on a score of 2-09 to 2-06. The second round saw a clash with Championship favourites Beragh at Omagh. Once again Greencastle confounded the experts and overcame the fancied side by 1-07 to 1-05. For the first time in quite a few years, the team reached the semi-final, where Drumragh were the opposition in Omagh. By now, Greencastle were favourites, but unfortunately a below par performance resulted in a one point defeat 0-08 to 1-04 to Drumragh, who went on to win the final easily. A case of so near yet so far. Evidently the club was now in a strong position and with an all-out effort, promotion may soon be clinched.