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.
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.