| First Round | Second Round | Third Round | Fourth Round |
| Fifth Round | Sixth Round | Semi Finals | FINAL |
FINAL
(At Firhill, Partick Thistle on Sunday 30th May 2000)
01 Whitburn
v Johnstone Burgh.................2*2, 4p3
Semi
Final (28th April 2000 & 5th May 2000)
01 Benburb
v Whitburn........................1*1, 2p3
02 Johnstone Burgh
v Shotts Bon Accord...............2*2, 3p0
Sixth
Round (11th March 2000)
01 Benburb
v Newtongrange Star....................2-1
02 Johnstone Burgh
v Cumnock Juniors......................2-1
03 Lanark United
v Shotts Bon Accord....................0-2
04 Whitburn
v Arbroath Sporting Club...............3-1
Fifth
Round (12th February 2000)
01 Benburb
v Larkhall Thistle.....................3-0
02 Cumnock Juniors
v Kilbirnie Ladeside...................3-1
03 Johnstone Burgh
v Glenafton Athletic...................2-1
04 Lanark United
v Thornton Hibs........................2-0
05 Maybole Juniors
v Arbroath Sporting Club...............0-3
06 Neilston
v Whitburn.............................2-3
07 Newtongrange Star v
Sunnybank............................2-0
08 Shotts Bon Accord v
Carnoustie Panmure..............2-2, 2-1
Fourth
Round (15th January 2000)
01 Benburb
v Royal Albert.........................4-1
02 Carnoustie Panmure v
Largs Thistle...................0-0, 2-0
03 Cumnock Juniors
v Kelty Hearts....................0-0, 2-1
04 Dundee Violet
v Newtongrange Star....................0-3
05 Inverurie Loco Works v Arbroath
Sporting Club...............2-4
06 Glenafton Athletic v
Glenrothes...........................6-0
07 Kilbirnie Ladeside v
Dundee North End.....................2-1
08 Lanark United
v Harthill Royal.......................4-1
09 Larkhall Thistle v
Broxburn Athletic....................3-1
10 Neilston
v Blantyre Victoria...............0-0, 3-1
11 Pollok
v Maybole Juniors......................0-1
12 Shettleston
v Johnstone Burgh......................0-3
13 Shotts Bon Accord v
Tayport..............................1-0
14 Sunnybank
v Fauldhouse United....................3-1
15 Thorniewood United v
Whitburn........................0-0, 0-4
16 Tranent
v Thornton Hibs........................0-1
Third
Round (4th December 1999)
01 Baillieston
v Royal Albert.........................1-4
02 Carnoustie Panmure v
Oakley United........................4-1
03 Cumbernauld United v
Broxburn Athletic...............1-1, 1-2
04 Cumnock Juniors
v FC Stoneywood........................3-0
05 Dundee North End v
West Calder United...................2-1
06 Dundee Violet
v Lesmahagow...........................2-1
07 Fauldhouse United v
Islavale.............................2-0
08 Forfar West End
v Tayport..............................0-2
09 Glenrothes
v Auchinleck Talbot....................2-1
10 Hill o' Beath Hawthorn v Newtongrange
Star...............2-2, 0-1
11 Johnstone Burgh
v Camelon..............................1-0
12 Kelty Hearts
v Stonehouse Violet....................2-0
13 Kilbirnie Ladeside v
Kinnoull.............................4-2
14 Kilwinning Rangers v
Benburb.........................0-0, 1*2
15 Largs Thistle
v Lochore Welfare......................1-0
16 Larkhall Thistle v
Craigmark Burntonians................5-2
17 Livingston
v Blantyre Victoria....................2-3
18 Lochee Harp
v Inverurie Loco Works.................0-3
19 Maryhill
v Neilston.............................0-1
20 Maybole Juniors
v Irvine Victoria......................3-0
21 Petershill
v Glenafton Athletic...................2-3
22 Pollok
v Bankfoot Athletic....................3-0
23 Pumpherston
v Whitburn.............................0-3
24 Renfrew
v Arbroath Sporting Club...............0-2
25 Shettleston
v Kello Rovers.........................5-1
26 Shotts Bon Accord v
Bo'ness United.......................2-1
27 St. Anthony's
v Harthill Royal.......................0-1
28 Sunnybank
v Kirkintilloch Rob Roy................5-3
29 Thorniewood United v
Aberdeen Lads Club...................6-0
30 Thornton Hibs
v Arthurlie.......................1-1, 3-2
31 Tranent
v Rutherglen Glencairn............2-2, 2-1
32 Troon
v Lanark United........................2-3
Second
Round (6th November 1999)
01 Aberdeen East End v
Craigmark Burntonians................1-2
02 Arbroath Sporting Club v Coupar Angus.........................4-0
03 Arbroath Vics
v Dundee North End.....................1-5
04 Ardrossan Winton Rovers v Lochore Welfare......................1-7
05 Arniston Rangers v
Benburb..............................0-2
06 Baillieston
v Annbank United.......................5-1
07 Banks o' Dee
v Livingston...........................2-3
08 Bathgate Thistle v
Thornton Hibs..............2-2, 1*1, 5p6
09 Bishopmill United v
West Calder United...................0-1
10 Blackburn United v
Carnoustie Panmure..............2-2, 1*4
11 Blairgowrie
v Lochee Harp..........................2-4
12 Blantyre Victoria v
Maud.................................2-0
13 Bonnybridge
v Kilbirnie Ladeside...................2-3
14 Brechin Vics
v Shotts Bon Accord....................0-5
15 Broughty Athletic v
FC Stoneywood........................0-6
16 Broxburn Athletic v
Musselburgh Athletic.......1-1, 2*2, 4p2
17 Camelon
v Dalkeith Thistle.....................4-3
18 Coltness United
v Shettleston.....................3-3, 1-2
19 Cruden Bay
v Bankfoot Athletic...............3-3, 1-2
20 Cumnock Juniors
v Hermes...............................4-1
21 Dunbar United
v Neilston.............................1-3
22 Dundee Violet
v Hurlford United......................1-0
23 Dyce
v Stonehouse Violet....................0-1
24 Forres Thistle
v Glenrothes...........................0-5
25 Glasgow Perthshire v
Bo'ness United.......................2-3
26 Glenafton Athletic v
Newburgh.............................4-2
27 Greenock
v Johnstone Burgh......................1-2
28 Hill o' Beath Hawthorn v Armadale Thistle.....................4-1
29 Inverurie Loco Works v New
Elgin............................7-1
30 Irvine Meadow X1 v
Whitburn........................2-2, 0-5
31 Irvine Victoria
v Downfield............................5-1
32 Kello Rovers
v Kirriemuir Thistle...................3-1
33 Kelty Hearts
v Beith Juniors........................3-0
34 Kilsyth Rangers
v Cumbernauld United...................0-1
35 Kilwinning Rangers v
Darvel Juniors.......................3-1
36 Kinnoull
v RAF Lossiemouth......................7-3
37 Kirkcaldy YM
v Fauldhouse United....................1-3
38 Kirkintilloch Rob Roy v Cambuslang
Rangers...................2-0
39 Lanark United
v Dunipace.............................5-0
40 Larkhall Thistle v
Edinburgh United.....................2-0
41 Lesmahagow
v Culter...............................2-1
42 Lochgelly Albert v
Islavale.............................2-6
43 Lugar Boswell Thistle v Aberdeen
Lads Club...................1-2
44 Luncarty
v Maybole Juniors......................1-3
45 Maryhill
v Fraserburgh..........................6-0
46 Montrose Roselea v
Forfar West End.................1-1, 1-2
47 Newtongrange Star v
Saltcoats Victoria...................2-1
48 Parkvale
v Largs Thistle........................1-7
49 Pollok
v Lochee United........................3-1
50 Pumpherston
v Lewis United.........................2-0
51 Renfrew
v Lossiemouth United...................9-2
52 Rutherglen Glencairn v Yoker
Athletic.......................4-3
53 Scone Thistle
v Petershill...........................1-7
54 St. Anthony's
v Ellon United.........................4-2
55 Steelend Victoria v
Harthill Royal.......................2-3
56 Stoneyburn
v Arthurlie............................0-6
57 Strathspey Thistle v
Royal Albert.........................0-1
58 Sunnybank
v East Kilbride Thistle................4-2
59 Thorniewood United v
Nairn St. Ninians....................7-1
60 Tranent
v Whitletts Victoria..................10-0
61 Troon
v Crossgates Primrose..................3-1
62 Vale of Clyde
v Auchinleck Talbot...............1-1, 0-2
63 Vale of Leven
v Oakley United...................2-2, 0-2
64 Wishaw
v Tayport..............................0-6
First
Round (9th October 1999)
01 Arbroath Victoria v
Banchory St. Ternan..................2-1
02 Ardeer Thistle
v Carnoustie Panmure..............0-0, 1-3
03 Armadale Thistle v
Rosyth Recreation....................1-0
04 Arthurlie
v Bonnyrigg Rose Athletic..............2-1
05 Ashfield
v Aberdeen East End....................2-4
06 Bankfoot Athletic v
Longside.............................3-2
07 Beith Juniors
v Bellshill Athletic...................1-0
08 Bishopmill United v
Buckie Rovers........................2-1
09 Blairgowrie
v St. Roch's...........................4-2
10 Bo'ness United
v Stonehaven...........................1-0
11 Camelon
v Buchanhaven Hearts...................3-1
12 Carluke Rovers
v Inverurie Loco Works............3-3, 2-3
13 Cumbernauld United v
Turriff United.......................3-1
14 Dalry Thistle
v Auchinleck Talbot....................0-4
15 Downfield
v Sauchie..............................2-1
16 Dundee East Craigie v
Bonnybridge..........................0-2
17 Dundee Violet
v Burghead Thistle....................10-1
18 Dundonald Bluebell v
Cruden Bay...........................0-1
19 Elmwood
v Glenrothes...........................0-6
20 Fochabers
v Tayport.............................0-13
21 Hall Russell United v
Lewis United.........................2-3
22 Irvine Meadow X1 v
Formartine United....................2-0
23 Irvine Victoria
v Forth Wanderers......................2-0
24 Islavale
v Muirkirk Juniors.....................1-0
25 Kinloss
v Dalkeith Thistle.....................1-6
26 Kirriemuir Thistle v
Glentanar............................5-0
27 Lanark United
v Port Glasgow.........................3-0
28 Largs Thistle
v Portgordon United....................4-0
29 Lochee United
v Tulliallan Thistle...................6-0
30 Maryhill
v Linlithgow Rose......................1-0
31 Montrose Roselea v
Forfar Albion...................2-2, 2-0
32 Newtongrange Star v
Haddington Athletic..................4-0
33 Oakley United
v Jeanfield Swifts.....................2-1
34 Saltcoats Victoria v
Deveronside..........................3-1
35 St. Andrews United v
Banks o' Dee.........................1-4