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 two preliminary rounds, five qualifying rounds, four proper rounds, and the semi-finals and final.
Round
Date
Extra preliminary round
Saturday 12 September 1908
Preliminary round
Saturday 19 September 1908
First qualifying round
Saturday 3 October 1908
Second qualifying round
Saturday 17 October 1908
Third qualifying round
Saturday 7 November 1908
Fourth qualifying round
Saturday 21 November 1908
Fifth qualifying round
Saturday 5 December 1908
First round proper
Saturday 16 January 1909
Second round
Saturday 6 February 1909
Third round
Saturday 20 February 1909
Fourth round
Saturday 6 March 1909
Semifinals
Saturday 27 March 1909
Final
Saturday 24 April 1909
Qualifying rounds
An extra preliminary round of seven ties, featuring 14 clubs from the north-west of England, was required at the beginning of this year's tournament to accommodate the growing popularity of association football in that region. The round included former Football League side Darwen and future League members Southport, Nelson and Macclesfield Town but Colne was the most successful club from this stage, progressing to the third qualifying round before losing to Accrington Stanley.
37 of the 40 clubs from the First and Second divisions joined the 12 clubs who came through the qualifying rounds. Of the League sides not given byes to this stage, Bradford Park Avenue was entered in the fourth qualifying round, but lost to Croydon Common in the fifth qualifying round, while Chesterfield and Gainsborough Trinity were entered in the fifth qualifying round.
Fifteen other non-league sides were given byes to the first round to bring the total number of teams up to 64. These were:
32 matches were scheduled to be played on Saturday, 16 January 1909, except for one game which was played three days later. Ten matches were drawn and went to replays in the following midweek fixture, of which one went to a second replay.
The sixteen second round matches were played on Saturday, 6 February 1909. Six matches were drawn, with the replays taking place in the following midweek fixture.
The four quarter final matches were scheduled for Saturday, 6 March 1909, although only two games were played on this date. The Burnley–Manchester United (the game was played 5 March and was abandoned for bad weather conditions after 72 minutes at 1-0 for Burnley) and Derby County–Nottingham Forest ties were played instead four and seven days later, respectively. The other two games were drawn, and replayed on 10 March.
The semi-final matches were played on Saturday, 27 March 1909. Bristol City and Derby County drew their match, and went on to replay it four days later. Bristol City won this tie, and so went on to meet the other semi-final winner, Manchester United, in the final.
^There are conflicting reports regarding the referee for the final. Most sources claim that the referee was a Mr. J. Mason, while others say it was Mr. T. P. Campbell