Georgian Cup 2008–09 is the sixty-fifth season overall and nineteenth since independence of the Georgian annual football tournament. The competition began on 30 August 2008 and will end with the Final held on 30 May 2009. The defending champions are Zestaponi.
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The first legs were played on 1 August and the second legs were played on 4 August 2008.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Meskheti Akhaltsikhe | 1–4 | Kolkheti-1913 Poti | 0–1 | 1–3 |
| Mglebi Zugdidi | 1–5 | Baia Zugdidi | 1–5 | 0–0 |
| Borjomi | 1–2 | Samtredia | 0–1 | 1–1 |
| Spartaki Tskhinvali | 11–0 | Ozurgeti | 5–0 | 6–0 |
| Magharoeli Chiatura | 4–1 | Torpedo Kutaisi | 1–1 | 3–0 |
| Meshakhte Tkibuli | 2–10 | Guria Lanchkhuti | 1–4 | 1–6 |
| Merani Martvili | 5–3 | Kolkheti Khobi | 4–0 | 1–3 |
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Olimpi Rustavi | 7–0 | Hereti Lagodekhi | 5–0 | 2–0 |
| Ameri Tbilisi | 4–1 | Kakheti Telavi | 2–1 | 2–0 |
| Sioni Bolnisi | 11–0 | Nortchi Dinamo | 4–0 | 7–0 |
| Lokomotivi Tbilisi | 10–3 | Aragvi Dusheti | 8–0 | 2–3 |
| Gagra | 2–7 | Tbilisi | 2–4 | 0–3 |
| Spartaki Tbilisi | 1–4 | Chikhura Sachkere | 1–0 | 0–4 |
In this round entered winners from the previous round as well as three teams that finished first, second and third in last year's Umaglesi Liga: Dinamo Tbilisi, WIT Georgia and Zestaponi. The first legs were played on August 30 and 31 and the second legs were played on September 16 and 17, 2008.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| WIT Georgia | 5–1 | Samtredia | 2–1 | 3–0 |
| Zestaponi | 5–1 | Chikhura Sachkere | 5–0 | 0–1 |
| Lokomotivi Tbilisi | 6–1 | Magharoeli Chiatura | 3–0 | 3–1 |
| Spartaki Tskhinvali | 2–3 | Merani Martvili | 1–0 | 1–3 |
| Dinamo Tbilisi | 10–1 | Tbilisi | 6–1 | 4–0 |
| Sioni Bolnisi | 4–1 | Kolkheti-1913 Poti | 3–0 | 1–1 |
| Ameri Tbilisi | 4–1 | Guria Lanchkhuti | 2–1 | 2–0 |
| Olimpi Rustavi | 5–1 | Baia Zugdidi | 1–1 | 4–0 |
The matches were played on 12 November (first legs) and 26 November 2008 (second legs).
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Lokomotivi Tbilisi | 5–4 | Sioni Bolnisi | 2–3 | 3–1 |
| WIT Georgia | 4–2 | Merani Martvili | 2–0 | 2–2 |
| Zestaponi | 0–1 | Dinamo Tbilisi | 0–0 | 0–1 (aet) |
| Olimpi Rustavi | 6–2 | Ameri Tbilisi | 3–0 | 3–2 |
The matches were played on 14 April (first legs) and 29 April 2009 (second legs).
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Olimpi Rustavi | 4–2 | WIT Georgia | 4–2 | 0–0 |
| Lokomotivi Tbilisi | 2–3 | Dinamo Tbilisi | 0–2 | 2–1 |
| 30 May 2009 16:00 UTC+4 |
Dinamo Tbilisi | 1 – 1 | Olimpi Rustavi | |
|---|---|---|---|---|
| Giorgi Nergadze | (Report) | Giorgi Megreladze | ||
| Penalties | ||||
| Giorgi Nergadze Levan Khmaladze |
2 – 0 |