The match is one of the few FA Cup Finals that has acquired a name; the Khaki Cup Final, owing to the large number of uniformed soldiers in attendance. However, the attendance of about 50,000 was lower than previous years as a result of wartime travel restriction and the mobilisation of large numbers of young men into the armed forces.
Chelsea had the easiest start in the FA Cup competition, their first round match was with Swindon Town, a Southern Football League team, but they made heavy work of it requiring a replay to defeat them and conceding 3 goals during the two matches. Their Cup performance improved considerably, and after defeating Arsenal (then a Second Division side ) in the second round, they defeated several First Division sides who finished above them in the league table, including Everton who later went on to win the league that season.
Sheffield defeated Blackpool, a second division side, in the first round and then made steady progress until round 4 where they met Oldham Athletic, who finished above them in the First Division that season, and they required a replay to finally defeat them. Sheffield met Bolton Wanderers in the semi-final and Utley, the Sheffield Captain, scored a rare goal.
Sheffield UnitedHome teams listed first.
Round 1: Blackpool 1–2 Sheffield United
Round 2: Sheffield United 1–0 Liverpool
Round 3: Sheffield United 1–0 Bradford
Round 4: Oldham Athletic 0–0 Sheffield United
Replay: Sheffield United 3–0 Oldham Athletic
Semi-final: Bolton Wanderers 1–2 Sheffield United
ChelseaHome teams listed first.
Round 1: Chelsea 1–1 Swindon Town
Replay: Chelsea 5–2 Swindon Town
Round 2: Chelsea 1–0 Arsenal
Round 3: Manchester City 0–1 Chelsea
Round 4: Chelsea 1–1 Newcastle
Replay: Newcastle 0–1 Chelsea
Semi-final: Everton 0–2 Chelsea
Chelsea were statistically the weaker side, whilst they had scored more goals than Sheffield in the league, their defence was poor and they had conceded many more and lay in the relegation zone. They had however beaten several strong clubs away from home during the FA cup competition and the programme noted that the underdogs had won on six occasions in the previous ten years. Chelsea also had injury problems: Bob Thomson, their leading goal scorer that season, had been injured in a league game at Bolton Wanderers ten days earlier and was doubtful. Vivian Woodward an amateur who played for Chelsea in peacetime, but was serving in the British Army, had been given leave to play in the final. However he refused to play and deny Thompson his part in the final which he had played so hard to reach. There was bad news when Thompson suffered an eye injury, but he played.
The programme showed that both teams played a 2-3-5 formation and the Chelsea teamsheet listed Vivian Woodward and Laurence Abrams in addition to those who played in the match. Neither played in the match.
The first goal was scored by Simmons just before half time. A ball in from the left hand side crossed over the Chelsea backs and Simmons, racing in from the right half, half-vollyed it into the top of the net. Some sources suggest that Molyneux should have stopped this goal but others state that he was let down by his defence in all three goals. Chelsea had their best chances just before half-time when they had two shots saved by Gough in the Sheffield goal.
At some point Chelsea woes were added to when Harry Ford on the right wing was injured.
Play was muted at the start of the second half as a thick fog descended over the pitch, preventing spectators from seeing any action on the opposite side of the pitch, though The Times commented that they were not missing much. The final two goals were scored in the last ten minutes. A shot from Wally Masterman rebounded from the bar but Fazackerly headed it past the Chelsea keeper for Sheffields second. Directly after this goal Joe Kitchen picked the ball up just inside the Chelsea half and passed two defenders. Molyneaux emerged from the Chelsea goal but Kitchen dodged him and placed the ball in the open net. At this point, before the final whistle, large numbers of the spectators began to leave.
The crowd included many men in uniform but a much larger contingent who, the Manchester Guardian commented, should have been in uniform. A number of wounded soldiers, one missing an arm, watched the match from lower stand.
The cup was awarded by the Earl of Derby whose speech, largely drowned out by a noisy crowd of young supporters, noted that all present needed to join together and play "a sterner game for England".
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