1999–2000 Georgian Cup
| Tournament details | |
|---|---|
| Country |  Georgia |
| Defending champions | Lokomotivi Tbilisi |
| Final positions | |
| Champions | Lokomotivi Tbilisi |
| Runner-up | Torpedo Kutaisi |
The 1999–2000 Georgian Cup (also known as the David Kipiani Cup) was the fifty-sixth season overall and ninth since independence of the Georgian annual football tournament.
Round of 16
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Torpedo Kutaisi | 7–0 | FC Academia | 5–0 | 2–0 |
| Lokomotivi Tbilisi | 2–1 | FC Tbilisi | 1–1 | 1–0 |
| Kolkheti-1913 Poti | 1–0 | Merani Tbilisi | 1–0 | 0–0 |
| Dinamo Batumi | 3–1 | Gorda Rustavi | 2–0 | 1–1 |
| WIT Georgia | 6–2 | TSU Tbilisi | 1–1 | 5–1 |
| Margveti Zestafoni II | 2–4 | Samgurali Tskhaltubo | 0–2 | 2–2 |
| Dila Gori | 5–1 | Zooweti Tbilisi II | 3–0 | 2–1 |
| Dinamo Tbilisi | 9–0 | Guria Lanchkhuti II | 6–0 | 3–0 |
Quarter-finals
The matches were played on 15 March (first legs) and 22 March 2000 (second legs).
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Dinamo Tbilisi | 8–1 | Dila Gori | 4–0 | 4–1 |
| Samgurali Tskhaltubo | 0–2 | Torpedo Kutaisi | 0–0 | 0–2 |
| WIT Georgia | 0–0 (pen. 1–3) | Lokomotivi Tbilisi | 0–0 | 0–0 |
| Dinamo Batumi | 3–0 | Kolkheti-1913 Poti | 3–0 | 0–0 |
Semi-finals
The matches were played on 2 May (first legs) and 9 May 2000 (second legs).
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Dinamo Tbilisi | 1–1 | Torpedo Kutaisi | 1–1 | 0–0 |
| Lokomotivi Tbilisi | 2–1 | Dinamo Batumi | 2–0 | 0–1 |
Final
| Lokomotivi Tbilisi | 0–0 (a.e.t.) | Torpedo Kutaisi |
|---|---|---|
| Penalties | ||
Gogichaishvili  Balashvili Yishkariani Khizanishvili |
4–2 | Asatiani Kvetenadze Chkhetiani Sheqriladze |