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. Some matches, however, might be rescheduled for other days if there were clashes with games for other competitions or the weather was inclement. 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 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
Round
Date
Extra preliminary round
Saturday 3 September 1927
Preliminary round
Saturday 17 September 1927
First round qualifying
Saturday 1 October 1927
Second round qualifying
Saturday 15 October 1927
Third round qualifying
Saturday 29 October 1927
Fourth round qualifying
Saturday 12 November 1927
First round proper
Saturday 26 November 1927
Second round proper
Saturday 10 December 1927
Third round proper
Saturday 14 January 1928
Fourth round proper
Saturday 28 January 1928
Fifth round proper
Saturday 18 February 1928
Sixth round proper
Saturday 3 March 1928
Semi-finals
Saturday 24 March 1928
Final
Saturday 21 April 1928
First round proper
At this stage 40 clubs from the Football League Third Division North and South joined the 25 non-league clubs who came through the qualifying rounds. Of those Third Division sides not playing in the first round proper, Millwall and Brentford were given byes to the third round, Barrow were entered into the fourth qualifying round (losing 3–1 to Workington), and Torquay United were not involved at any stage of the competition. To make the number of matches up, non-league Northfleet United, Aberdare Athletic and Leyton were given byes to this round. 34 matches were scheduled to be played on Saturday, 26 November 1927. Six matches were drawn and went to replays in the following midweek fixture.
The 44 First and Second Division clubs, entered the competition at this stage, along with Third Division Millwall and Brentford. Also given a bye to this round of the draw were amateur side Corinthian. The matches were scheduled for Saturday, 14 January 1928. Three matches were drawn and went to replays in the following midweek fixture.
The semi-final matches were played on Saturday, 24 March 1928. The Huddersfield Town–Sheffield United local derby tie went to two replays before it was settled in Huddersfield's favour. Huddersfield went on to meet Blackburn Rovers in the final at Wembley.