1961-62 FA Youth Cup
From TheChels.info - The Chelsea Football Club Wiki
| D | M | Year | Round | Opposition | Venue | Score | Scorers | Additional information |
| 16 | Sep | 1961 | Playoff | Gorleston | Home | 10-0 | Bill (5), Hollins (2), Scott, Harris, Huxford (pen) | |
| 3 | Oct | 1961 | First | Cator Rovers | Away | 8-0 | Scott (3), Bill (2), Vafiadis (2), Gillingwater | |
| 4 | Nov | 1961 | Second | Ipswich Town | Home | 3-0 | Scott, Bateman (pen) | |
| 17 | Jan | 1962 | Third | Arsenal | Away | 2-1 | Scott, Gillingwater | |
| 10 | Feb | 1962 | Fourth | Cambridge United | Away | 3-0 | Gillingwater (3) | |
| 3 | Mar | 1962 | Fifth | West Ham United | Home | 2-1 | Gillingwater, Vafiadis | |
| 31 | Mar | 1962 | Semi Final (First Leg) | Wolverhampton Wanderers | Home | 0-1 | ||
| 11 | Apr | 1962 | Semi Final (Second Leg) | Wolverhampton Wanderers | Away | 0-3 | Chelsea lost 4-0 on aggregate |