1999–2000 Scottish Junior Cup
| Tournament details | |
|---|---|
| Country |  Scotland |
| Teams | 163 |
| Defending champions | Kilwinning Rangers |
| Final positions | |
| Champions | Whitburn |
| Runner-up | Johnstone Burgh |
| Tournament statistics | |
| Matches played | 162 (not including replays) |
The 1999–00 Scottish Junior Cup was a competition in Scottish Junior football. It was won by Whitburnafter they defeated Johnstone Burgh 4–3 on penalties after drawing 2–2 in the final.
First round
These ties were scheduled to take place on Saturday 9 October 1999.
| Home Team | Score | Away Team |
|---|---|---|
Second round
These ties were scheduled to take place on Saturday 6 November 1999.
| Home Team | Score | Away Team |
|---|---|---|
Third round
These ties were scheduled to take place on Saturday, 4 December 1999
| Home Team | Score | Away Team |
|---|---|---|
Fourth round
These ties were scheduled to take place on Saturday, 15 January 2000.
| Home Team | Score | Away Team |
|---|---|---|
Fifth round
These ties were scheduled to take place on Saturday, 12 February 2000.
| Home Team | Score | Away Team |
|---|---|---|
| Benburb | 3 – 0 | Larkhall Thistle |
| Cumnock Juniors | 3 – 0 | Kilbirnie Ladeside |
| Johnstone Burgh | 2 – 1 | Glenafton Athletic |
| Lanark United | 2 – 0 | Thornton Hibs |
| Maybole Juniors | 3 – 0 | Arbroath Sporting Club |
| Neilston | 2 – 3 | Whitburn |
| Newtongrange Star | 2 – 0 | Sunnybank |
| Shotts Bon Accord | 2 – 2 | Carnoustie Panmure |
| replay | 2 – 1 |
Quarter finals
These ties were played on Saturday 11 March 2000.
| Home Team | Score | Away Team |
|---|---|---|
| Benburb | 2 – 1 | Newtongrange Star |
| Johnstone Burgh | 2 – 1 | Cumnock Juniors |
| Lanark United | 0 – 2 | Shotts Bon Accord |
| Whitburn | 3 – 1 | Arbroath Sporting Club |
Semi-Finals
These ties were played on 28 April 2000 & 5 May 2000, respectively.
| Home Team | Score | Away Team | Venue |
|---|---|---|---|
| Benburb | 1 – 1 | Whitburn | |
| Johnstone Burgh | 2 – 2 | Shotts Bon Accord |
Final
The final took place on Sunday 30 May 2000.
| Home Team | Score | Away Team | Venue |
|---|---|---|---|
| Whitburn | 2 – 2 | Johnstone Burgh | Firhill, Partick Thistle |