Matches were scheduled to be played at the stadium of the team named first on the date specified for each round, which was always a Saturday. If scores were level after 90 minutes had been played, a replay would take place at the stadium of the second-named team later the same week. If the replayed match was drawn further replays would be held at neutral venues until a winner was determined. If scores were level after 90 minutes had been played in a replay, a 30-minute period of extra time would be played.
Calendar
The format of the FA Cup for the season had a preliminary round, five qualifying rounds, three proper rounds, and the semi-finals and final.
Round
Date
Preliminary round
Saturday 24 September 1898
First round qualifying
Saturday 1 October 1898
Second round qualifying
Saturday 15 October 1898
Third round qualifying
Saturday 29 October 1898
Fourth round qualifying
Saturday 19 November 1898
Fifth round qualifying
Saturday 10 December 1899
First round proper
Saturday 28 January 1899
Second round proper
Saturday 11 February 1899
Third round proper
Saturday 25 February 1899
Semi-finals
Saturday 18 March 1899
Final
Saturday 15 April 1899
First round proper
This season saw the further expansion of the Football League First and Second Divisions to 18 teams each. Once again, the FA Cup's first round proper contained sixteen ties between 32 teams with the 18 First Division sides given a bye to this round, along with Newton Heath, Woolwich Arsenal and Manchester City from the Second Division. In recognition of the increasing strength of the Southern League, the previous season's champions of that competition Southampton were awarded the final automatic entry to this stage.
Most of the other Football League clubs were entered into the third qualifying round, with the exceptions of Barnsley, who started in the second qualifying round, and Burton Swifts, Blackpool and Loughborough who were placed in the first qualifying round. Of those sides, only Grimsby Town, Small Heath and Glossop North End progressed to the FA Cup proper along with non-league sides Jarrow, South Shore, Heanor Town, Kettering, Bristol City, New Brompton and Tottenham Hotspur. Jarrow, Bristol City and New Brompton were featuring in the first round for the first time, but, in a further reflection of the growing stature of the Southern League, Southampton and Tottenham Hotspur were the only non-league clubs to progress beyond this stage.
The matches were played on Saturday, 28 January 1899. Four matches were drawn, with the replays taking place in the following midweek fixture.
The eight Second Round matches were scheduled for Saturday, 11 February 1899, although only three games were played on this date. The other five games were played the following Saturday. There were three replays, played in the following midweek fixture.
The semi-final matches were both played on Saturday, 18 March 1899. The Sheffield United–Liverpool match went to a replay, played the following Thursday. The match was again replayed a week later, when Sheffield managed a 1–0 win. They went on to meet Derby County in the final at Crystal Palace.
The final took place on Saturday, 15 April 1899 at Crystal Palace. Just under 74,000 supporters attended the match, a record attendance at the time. John Boag opened the scoring for Derby County after 12 minutes. Derby's lead was maintained until midway through the second half, until Sheffield struck back with three goals in ten minutes from Walter Bennett, Billy Beer and John Almond. Fred Priest scored the fourth and final goal in the eighty-ninth minute, to cap a good victory for the Yorkshire side.
