There were 29 entrants in the 1874–75FA Cup, one more than the previous year. One team got a bye in the first round, meaning that the second round consisted of 15 teams. The Old Etonians received a bye in the second round, therefore the quarter-finals had the standard eight teams.
The Engineers, who lost the final on two of the three previous occasions, kicked off with a resounding 3–0 win over Marlow. They kept the scoring feat up in the next round, beating Cambridge University 5–0. The Quarter Final was a closely fought match against Clapham Rovers, just prevailing 3–2. The Semi-final produced a repeat fixture of the final of 1874, as the Engineers faced Oxford University. This time, the Engineers won 1–0.
The Old Etonians started off against the Swifts, which proved a very tough match. After two drawn games, the Etonians managed to pull off a 3–0 victory. In the second round they received a bye which led them into the quarter-finals. Following a win against Maidenhead, they played Shropshire Wanderers. An extremely close match was just edged out by a single goal to nil.
The first match was notable chiefly because it was played in a "howling gale". The conditions considerably favoured the Etonians team, which had the wind at its backs for all but 10 minutes of the 90, and all 30 minutes of extra time (teams in this period changed ends after every goal- this game was the last to feature this rule).Cuthbert Ottaway received a severe hack on his ankle 37 minutes into the final and was forced to leave the field; in his absence, the Old Boys were regarded as fortunate to have held on for a 1–1 draw.
Ottaway failed to recover in time for the replay, held only three days later, and Etonians also lost the services of three other players who had prior commitments. Unable to obtain adequate replacements, the Old Boys arrived at the ground an hour late and lost the delayed replay 0–2.