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The 1999–2000 Liechtenstein Cup was the fifty-fifth season of Liechtenstein's annual cup competition. Seven clubs competed with a total of fifteen teams for one spot in the qualifying round of the UEFA Cup. Defending champions were FC Vaduz, who have won the cup continuously since 1998.
| Tournament details | |
|---|---|
| Country | Liechtenstein |
| Final positions | |
| Champions | FC Vaduz |
| Runner-up | FC Balzers |
| Team 1 | Score | Team 2 |
|---|---|---|
| 19 October 1999 | ||
| FC Triesen II | 3–3 (a.e.t.) (4–3 p) |
FC Schaan Azzuri |
| FC Triesen | 1–1 (a.e.t.) (2–1 p) |
FC Vaduz II |
| FC Balzers II | 2–1 | FC Triesenberg |
| FC Triesenberg II | 0–9 | FC Balzers |
| 20 October 1999 | ||
| USV Eschen/Mauren II | 0–3 | FC Schaan |
| FC Ruggell II | 2–4 (a.e.t.) | USV Eschen/Mauren |
| FC Vaduz III | 3–0 | FC Ruggell |
| Team 1 | Score | Team 2 |
|---|---|---|
| 9 November 1999 | ||
| FC Vaduz III | 0–2 | FC Balzers |
| FC Triesen II | 0–22 | FC Vaduz |
| 2 March 2000 | ||
| FC Triesen | 2–1 | USV Eschen/Mauren |
| 5 April 2000 | ||
| FC Balzers II | 1–2 | FC Schaan |
| Team 1 | Score | Team 2 |
|---|---|---|
| 11 April 2000 | ||
| FC Schaan | 2–2 (a.e.t.) (7–8 p) |
FC Balzers |
| 12 April 2000 | ||
| FC Triesen | 0–3 | FC Vaduz |
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