SEASON 1898/99
First Round
Portmadoc
2-5
Bangor
Holywell
0-3
Carnarvon Ironopolis
Rhyl United
3-2
Llandudno Swifts
Flint
bye
 
Chirk
7-0
Rhos Eagle Wanderers
Buckley Victoria
bye
 
Caergwrle Wanderers
bye
 
Mold Town
bye
 
Oswestry United 13-0
13-0
Llanidloes
Newport
1-0
Aberystwyth Town
Ironbridge
6-2
Knighton
Wem
3-1
Welshpool United
Barry Dock
4-1
Builth
Blaina Town
1-7
Aberdare
Brecon
bye
 
Rogerstone
v
Rhayader (withdrew)
Druids
bye
 
Wrexham
bye
 
Newtown
bye
 
Wellington Town
bye
 
Second Round
Bangor
3-1
Carnarvon Ironopolis
Rhyl United
2-0
Flint
Mold Town
0-5
Chirk
Caergwrle Wanderers
1-2
Buckley Victoria
Oswestry United
6-1
Ironbridge
Newport (w/o)
v
Wem (withdrew)
Brecon (withdrew)
v
Rogerstone (w/o)
Barry Dock
3-2
Aberdare
Third Round
Bangor
1-1
Rhyl United
Rhyl disqualified - ineligble player
Buckley Victoria
1-2
Chirk
Newport
1-4
Oswestry United
Barry Dock
2-1
Rogerstone
Fourth Round
Newtown (w/o)
v
Wellington Town (withdrew)
Oswestry
2-2
Chirk
replay 1-2 aet
Wrexham
7-1
Barry Dock
Druids
5-2
Bangor
Semi-finals
Wrexham
1-0
Chirk
at Wynnstay Park, Ruabon
Druids
4-0
Newtown
at Oswestry
Final
Druids
on 11 April 1899
Druids
on 15 April 1899, both matches at Chirk