FA Cup 1978/79, Preliminary Round |
 | | | Fareham Town | – | Cowes | | 2:0 * |
| |
FA Cup 1978/79, Preliminary Round |
| | | Cowes | – | Fareham Town | | 0:0 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Salisbury | – | Cowes | | 5:1 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Waterlooville | – | Cowes | | 9:0 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Cowes | – | Gosport Borough | | 0:2 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Salisbury | – | Cowes | | 3:0 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Alton Town | – | Cowes | | 2:0 |
| |
FA Cup 1972/73, Preliminary Round |
| | | Newport IOW | – | Cowes | | 2:0 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Alton Town | – | Cowes | | 3:2 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Cowes | – | Basingstoke Town | | 1:3 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Fareham Town | – | Cowes | | 3:0 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Cowes | – | Thornycroft Athletic | | 0:1 |
| |
FA Cup 1967/68, Second Qualifying Round |
| | | Salisbury | – | Cowes | | 5:1 * |
| |
FA Cup 1967/68, Second Qualifying Round |
| | | Cowes | – | Salisbury | | 1:1 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Cowes | – | Thornycroft Athletic | | 2:1 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Salisbury | – | Cowes | | 4:1 |
| |
FA Cup 1965/66, Third Qualifying Round |
| | | Fareham Town | – | Cowes | | 4:2 |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Newport IOW | – | Cowes | | 0:3 * |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Cowes | – | Newport IOW | | 3:3 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Chichester City | – | Cowes | | 3:6 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Basingstoke Town | – | Cowes | | 4:2 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Cowes | – | Chichester City | | 5:4 |
| |
FA Cup 1963/64, Fourth Qualifying Round |
| | | Yeovil Town | – | Cowes | | 1:0 |
| |
FA Cup 1963/64, Third Qualifying Round |
| | | Cowes | – | Basingstoke Town | | 3:1 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Cowes | – | Andover | | 4:2 * |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Andover | – | Cowes | | 1:1 |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Cowes | – | Alton Town | | 5:1 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Andover | – | Cowes | | 4:1 |
| |
FA Cup 1961/62, Third Qualifying Round |
| | | Andover | – | Cowes | | 2:1 |
| |
FA Cup 1961/62, Second Qualifying Round |
| | | Cowes | – | Newport IOW | | 5:1 * |
| |
FA Cup 1961/62, Second Qualifying Round |
| | | Newport IOW | – | Cowes | | 0:0 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Cowes | – | Newbury Town | | 3:1 |
| |
FA Cup 1960/61, Second Qualifying Round |
| | | Chichester City | – | Cowes | | 6:3 |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Newport IOW | – | Cowes | | 1:2 |
| |
FA Cup 1959/60, Third Qualifying Round |
| | | Basingstoke Town | – | Cowes | | 2:1 |
| |
FA Cup 1959/60, Second Qualifying Round |
| | | Cowes | – | Andover | | 3:0 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Cowes | – | Newport IOW | | 2:0 |
| |
FA Cup 1958/59, Second Qualifying Round |
| | | Cowes | – | Alton Town | | 1:2 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Cowes | – | Chichester City | | 5:4 |
| |
FA Cup 1957/58, Fourth Qualifying Round |
| | | Trowbridge Town | – | Cowes | | 4:1 * |
| |
FA Cup 1957/58, Fourth Qualifying Round |
| | | Cowes | – | Trowbridge Town | | 2:2 |
| |
FA Cup 1957/58, Third Qualifying Round |
| | | Cowes | – | Chichester City | | 3:1 |
| |
FA Cup 1957/58, Second Qualifying Round |
| | | Basingstoke Town | – | Cowes | | 2:5 |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Winchester City | – | Cowes | | 0:1 * |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Cowes | – | Winchester City | | 0:0 |
| |
FA Cup 1956/57, First Qualifying Round |
| | | Cowes | – | Gosport Borough Athletic | | 1:4 |
| |
FA Cup 1955/56, Second Qualifying Round |
| | | Cowes | – | Fareham Town | | 2:3 |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Cowes | – | Bournemouth Gasworks Athletic | | 4:1 |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Gosport Borough Athletic | – | Cowes | | 2:1 |
| |
FA Cup 1954/55, First Qualifying Round |
| | | Cowes | – | Chichester City | | 6:0 |
| |
FA Cup 1953/54, Third Qualifying Round |
| | | Newport IOW | – | Cowes | | 4:2 |
| |
FA Cup 1953/54, Second Qualifying Round |
| | | Cowes | – | Alton Town | | 5:0 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Cowes | – | Newport IOW | | 0:1 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Basingstoke Town | – | Cowes | | 4:3 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Bournemouth Amateurs | – | Cowes | | 4:2 * |
| |
FA Cup 1950/51, Preliminary Round |
| | | Cowes | – | Bournemouth Amateurs | | 1:1 |
| |
FA Cup 1949/50, Third Qualifying Round |
| | | Cowes | – | Weymouth | | 1:5 |
| |
FA Cup 1949/50, Second Qualifying Round |
| | | Cowes | – | Bournemouth Amateurs | | 4:0 * |
| |
FA Cup 1949/50, Second Qualifying Round |
| | | Bournemouth Amateurs | – | Cowes | | 3:3 |
| |
FA Cup 1949/50, First Qualifying Round |
| | | Cowes | – | Dorchester Town | | 5:1 |
| |
FA Cup 1949/50, Preliminary Round |
| | | Pirelli General Cables | – | Cowes | | 3:4 |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Cowes | – | Lymington | | 4:0 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Cowes | – | East Cowes Victoria | | 1:2 |
| |
FA Cup 1947/48, Extra Preliminary Round |
| | | Cowes | – | Newport IOW | | 1:3 |
| |
FA Cup 1946/47, Preliminary Round |
| | | RAOC Hilsea | – | Cowes | | 4:3 |
| |
FA Cup 1945/46, Third Qualifying Round |
| | | Newport IOW | – | Cowes | | 0:1 * |
| |
FA Cup 1945/46, Second Qualifying Round |
| | | Cowes | – | East Cowes Victoria | | 4:2 |
| |
FA Cup 1945/46, First Qualifying Round |
| | | Ryde Sports | – | Cowes | | 1:3 |
| |
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