FA Cup 2023/24, Preliminary Round |
 | 19.08.2023 |  | Sheffield | – | Skegness Town | | 2:1 (2:1) |
| Dronfield |
FA Cup 2022/23, Preliminary Round |
| 20.08.2022 | | Anstey Nomads | – | Skegness Town | | 5:2 (2:2) |
| Anstey |
FA Cup 2021/22, Preliminary Round |
| 21.08.2021 | | Anstey Nomads | – | Skegness Town | | 2:1 (1:1) |
| Anstey |
FA Cup 1985/86, First Qualifying Round |
| | | Goole Town | – | Skegness Town | | 3:2 |
| |
FA Cup 1983/84, Preliminary Round |
| | | Skegness Town | – | Tividale | | 2:4 |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Irthlingborough Diamonds | – | Skegness Town | | 1:0 * |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Worksop Town | – | Skegness Town | | 2:1 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Boston United | – | Skegness Town | | 3:0 |
| |
FA Cup 1979/80, Third Qualifying Round |
| | | Boston | – | Skegness Town | | 1:0 * |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Skegness Town | – | Louth United | | 0:1 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | March Town United | – | Skegness Town | | 2:1 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Skegness Town | – | Wisbech Town | | 0:2 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Skegness Town | – | Retford Town | | 0:2 * |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Skegness Town | – | Boston | | 1:2 * |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Skegness Town | – | Wisbech Town | | 2:3 |
| |
FA Cup 1972/73, Third Qualifying Round |
| | | Kettering Town | – | Skegness Town | | 7:0 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | King's Lynn | – | Skegness Town | | 4:1 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Skegness Town | – | Spalding United | | 1:2 * |
| |
FA Cup 1969/70, Second Qualifying Round |
| | | King's Lynn | – | Skegness Town | | 2:1 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Skegness Town | – | King's Lynn | | 0:3 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Skegness Town | – | King's Lynn | | 0:2 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | King's Lynn | – | Skegness Town | | 4:3 |
| |
FA Cup 1965/66, Third Qualifying Round |
| | | Skegness Town | – | Grantham | | 0:7 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Skegness Town | – | Spalding United | | 0:3 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Skegness Town | – | Stamford | | 2:4 |
| |
FA Cup 1962/63, Third Qualifying Round |
| | | Boston United | – | Skegness Town | | 1:0 |
| |
FA Cup 1961/62, Third Qualifying Round |
| | | Grantham | – | Skegness Town | | 3:1 |
| |
FA Cup 1960/61, Third Qualifying Round |
| | | Holbeach United | – | Skegness Town | | 1:0 |
| |
FA Cup 1959/60, Third Qualifying Round |
| | | Gainsborough Trinity | – | Skegness Town | | 3:0 * |
| |
FA Cup 1958/59, Second Qualifying Round |
| | | Skegness Town | – | Boston United | | 0:3 |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Grantham | – | Skegness Town | | 2:0 * |
| |
FA Cup 1956/57, First Qualifying Round |
| | | Grantham | – | Skegness Town | | 2:1 |
| |
FA Cup 1955/56, First Round Proper |
| 19.11.1955 | | Skegness Town | – | Worksop Town | | 0:4 |
| |
FA Cup 1954/55, Third Qualifying Round |
| | | Skegness Town | – | Boston United | | 2:6 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Brigg Town | – | Skegness Town | | 4:1 |
| |
FA Cup 1952/53, Third Qualifying Round |
| | | Boston United | – | Skegness Town | | 3:2 |
| |
FA Cup 1951/52, Fourth Qualifying Round |
| | | Rawmarsh Welfare | – | Skegness Town | | 4:2 |
| |
FA Cup 1950/51, Extra Preliminary Round |
| | | Skegness Town | – | Boston United | | 3:10 |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Alford United | – | Skegness Town | | 6:4 |
| |
