Irish Football Association Challenge Cup

1881- Moyola Park
Moyola Park Association Football Club was formed during season 1879/1880 under the patronage of Lord Spencer Chichester, the landlord of the Moyola Park estate. Their  first recorded game was a friendly at home against Cliftonville FC, Belfast on 14 February 1880, in which the visitors recorded a 3-0 victory. Lord Spencer Chichester was the inaugural president of the fledgling Irish Football Association, which was formed in November 1880. On 9 April 1881 Moyola Park became the first winners of the Irish Football Association's Challenge Cup, defeating Cliftonville by 1-0 in the final, from an initial entry of seven clubs, the founder members of the Association. The gate receipts on that day were £8-00. 

1882- Queen's Island 

I can find out very little about the Belfast based Queen's Island side, other than that they fielded 10 Scotsmen in the final. Cliftonville were runners up again, Queen's Island winning 1-0 in front of a crowd of  2,000 at the Prospect ground. 

1883- Cliftonville 

Having been runners up in the first two finals Cliftonville finally got their name on the trophy with a comfortable 5-0 win over Ulster. 

1884- Distillery
Distillery won their first cup with a 5-0 win over Wellington Park. The distillery full backs were club captain Matt 'Daddy' Wilson and his son Bob Wilson. Distillery were founded in 1880 and were based at West Belfast's Distillery Street.

1885 - Distillery

Distillery defended their title with 9 of the previous year's winning side making a return to the final. This time round  Limavady were beaten 3-0. The finals were still attracting crowds of about 2,000 at this time. 

1886-  Distillery

3 in a row for Distillery. Limvady were beaten 1-0 and protested following a very rough final. The Irish FA apportioned equal blame for the violence of the match to both sides. The result stood but the cup and medals were withheld.

1887- Ulster 

new name on the cup as Ulster overcame Cliftonville 3-1 at Belfast's Broadway with 4,000 in attendance. 

1888- Cliftonville

Bob Wilson won his 4th Irish Cup playing against his former club, Distillery,  as Cliftonville ran out 2-1 winners.

1889- Distillery

Outsiders Belfast YMCA excelled themselves and lost the final to the strongest team in Ireland by the odd goal in 9! Having taken the lead in the first minute YMCA camer back from 4-2 down but Distillery's 5th goal proved too much for them. 

1890-  Gordon Highlanders 

Gordon Highlanders was a Scottish regiment in the British Army. They took advantage of their Irish posting to win the cup, beating Cliftonville in the final. Unsurprisingly the Highlander's XI was entirely Scottish. 4 of the Cliftonville side had played for YMCA in the previous tear's final. 
The first match was drawn 2-2, the Highlander's winning the replay 3-0. Highlander's Bob Milne settled in Belfast and for many years played for Linfield . He also represented  Ireland at international level. 

1891- Linfield

Milne was back, winning the cup with Linfield. Linfield became the first club to win the 'double' in Ireland  In the final they beat Ulster 4-2 at Solitude. The attendance was 5,000. The Ulster team featured Jack Reynolds, who was capped by both Ireland and England. 

1892- Linfield

Linfield retained the trophy by thrashing army side  Black Watch 7-0 in the final. Black Watch fielded XI Scotsmen. Stangley Bob Hill, who scored 4 goals in the final was a Scotsman who had once served with the Black Watch! Linfield also featured William Arnott, brother of the Scottish international Walter Arnott. Some sources credit his cup win with Linfield to Walter. 

1893- Linfield
Linfield secured a hat trick of 'doubles' beating Cliftonville 5-1 in the cup final. 

1894- Distillery 3 Linfield 2

Distillery were the first Irish team to use a coach (Adam Wright). The final played on St Patrick's Day  ended in a 2-2 draw,Distillery playing the second half with 10 men after Davy Brown broke his leg.
In the replay one month later it was Linfield who were reduced to 10 early on, with stalwart Bob Milne being the injured party. Distillery won 3-2.

Bob Milne
1895- Linfield 
Linfield  smashed Dublin based Bohemians 10-1 in the final, this after Bohemians had taken the lead.   Joe McAllen and Bob Milne scored three goals each. Milne had now scored in the final for 3 seasons in a row and played in 8 final ties altogether (including replays).

1896- Distillery 

 Distillery beat  Glentoran 3-1 at Belfast's Solitude, the attendance was 6,000. 

1897- Cliftonville
For the third time an army team reached the final. This time it was the Sherwood Foresters,an English regiment based in Dublin's Curragh. The Foresters fielded an XI made up entirely of Englishmen. Cliftonville won 3-1. 

1898- Linfield
 A return to winning ways for Linfield, double winners again this season. In the cup final they beat  St. Columb's Hall Celtic (Derry) by 2- 0. Bob Milne was there, of course.

1899- Linfield
A crowd of 7,000 at Solitude saw 85 minutes of football before Glentoran walked off the pitch, incensed at the refusal of a penalty. Linfield were 1-0 up at the time, and the Irish FA decided that the score should stand. 
Bob Milne made his 10th appearance in the cup final (a further 2 would follow).

1900- Cliftonville 
A Belfast v Dublin final saw Cliftonville beat Bohemians 2-1.
Cliftonville had received a bye to the final when their opposition, The Kings Own Scottish Borderers  a regimental team, were called up for the Boer War in South Africa.