La Churchill Cup era una competizione calcistica regionale disputata dalle squadre delle Contee di Dumfriesshire, Wigtownshire e Kirkcudbrightshire. Fino all'introduzione della Southern Counties Cup era la competizione più importante del sud della Scozia. Prendeva il nome dal Rev. A. Churchill che aveva donato il trofeo.

 

1881-82 Moffat e Dumfries 5TH KIRKCUDBRIGHT RV 5th KRV - Newton Stewart A. 3-3 (replay 1-1 d.t.s.) titolo condiviso
    NEWTON STEWART ATHLETIC
1882-83 Maxwelltown VALE OF NITH Vale of Nith - Volunteer Athletic 1-0
1883-84 Dumfries e Stranraer 5TH KIRKCUDBRIGHT RV 5th KRV - Stranraer 3-3 (replay 1-0)
1884-85 Dumfries QUEEN OF THE SOUTH WANDERERS Queen of the South Wanderers - Stranraer 6-1
1885-86 Moffat e Dumfries QUEEN OF THE SOUTH WANDERERS Moffat - Queen of the South Wanderers 4-4 (replay 1-11)
1886-87 Dumfries MID-ANNANDALE Mid-Annandale - Vale of Nith 4-3
1887-88 Moffat e Dumfries MOFFAT Moffat - Mid-Annandale 4-4 (replay 7-6)
1888-89 Moffat 5TH KIRKCUDBRIGHT RV Mid-Annandale - 5th KRV 2-2 (replay 2-4)
1889-90 Dumfries MOFFAT Moffat - Newton Stewart Athletic 1-0
1890-91 Dumfries 5TH KIRKCUDBRIGHT RV 5TH KRV - Newton Stewart Athletic 13-0
1891-92 Moffat MID-ANNADALE Mid-Annandale - 5th Kirkcudbright RV 3-1
1892-93 Dumfries QUEEN OF THE SOUTH WANDERERS Queen of the South Wanderers - Newton Stewart Athletic 6-0
1893-94 Newton Stewart 5TH KIRKCUDBRIGHT RV 5th KRV - Garliestown 7-0
1894-95 Dumfries 5TH KIRKCUDBRIGHT RV 5th KRV - Maxwelltown Thistle 3-2