SEASON 1899/00
First Round
Ironbridge (w/o)
v
Wem (withdrew)
Aberdare
2-0
Barry Dock
Portmadoc, Carnarvon Ironopolis, Rhyl United, Buckley Victoria, Flint, Welshpool, Towyn, Newport, Rhayader, Knighton, Builth, Llandrindod Wells, Rogerstone, Druids, Chirk, Newtown, Wrexham, Llandudno Swifts, Bangor, Oswestry United, Aberystwyth Town all received byes.
Second Round
Carnarvon Ironopolis
5-0
Portmadoc
Rhyl United
bye
 
Buckley Victoria
3-1
Flint
Welshpool
5-0
Towyn
Newport
v
Ironbridge
tie awarded to Newport
Rhayader
2-1
Knighton
Builth
0-1
Llandrindod Wells
abandoned but score allowed to stand
Rogerstone
0-2
Aberdare
Third Round
Newtown
6-1
Llandudno Swifts
Oswestry United (w/o)
v
Wrexham (withdrew)
Bangor (w/o)
v
Llandrindod Wells (withdrew)
Rhayader
0-1
Aberystwyth Town
Druids 2-0
2-0
Chirk
Buckley Victoria (w/o)
v
Newport (withdrew)
Carnarvon Ironopolis
4-2
Welshpool
Rhyl United
2-1
Aberdare
Fourth Round
Oswestry United
1-1
Rhyl United
protest ineligible player Rhyl dismissed
Aberystwyth Town
1-0
Newtown
Bangor
0-4
Druids
Carnarvon Ironopolis
2-1
Buckley Victoria
Semi-finals
Aberystwyth Town
1-0
Carnarvon Ironopolis
at Oswestry
replay 2-0 at Towyn
Druids
2-0
Oswestry United
at Chirk
Final
Druids
on 16 April 1900 at Newtown