Belarusian Cup 2008–09 is the eighteenth season of the Belarusian annual cup competition. Contrary to the league season, it is conducted in a fall-spring rhythm. The first games were played on July 30, 2008. Winners of the Cup will qualify for the UEFA Europa League second qualifying round.
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A premiliary round was held in order to reduce the number of teams in the First Round to 32. The matches were played on July 30, 2008.
| Team 1 | Score | Team 2 |
|---|---|---|
| KZAL Minsk (A) | 0–10 | DSK Gomel (III) |
| Chaussy (A) | 4–1 | Livadia Dzerzhinsk (III) |
All fourteen teams of the First League and most of Second League teams plus three more amateur teams started in this round. They were joined by two winners of Preliminarly Round. The games were played on July 30, except two games with Preliminarly Round winners, which were held on August 3 and August 6.
| Team 1 | Score | Team 2 |
|---|---|---|
| PMK-7 Gantsevichi (A) | 0–3 | Slavia-Mozyr (II) |
| Gorodeya (III) | 1–2 | Dinamo-Belcard Grodno (II) |
| Zhlobin (III) | 2–5 | Vedrich-97 Rechytsa (II) |
| Neftianik Rechytsa (A) | 0–1 | Lida (II) |
| BGATU-Niva Samokhvalovichi (III) | 0–2 | PMC Postavy (II) |
| Orsha (III) | 0–3 | Veras Nesvizh (II) |
| Neman Mosty (III) | 2–0 | Baranovichi (II) |
| Zvezda-BGU Minsk (III) | 1–0 | Slutsksakhar Slutsk (III) |
| Osipovichi (III) | 5–3 | Polotsk (II) |
| Molodechno (III) | 1–3 | Volna Pinsk (II) |
| Tsementnik Volkovysk Raion (A) | 1–7 | Kommunalnik Slonim (II) |
| Start Miory (A) | 1–6 (aet) | Khimik Svetlogorsk (II) |
| Klechesk Kletsk (III) | 0–0 (aet, p.4–2) | Spartak Shklov (II) |
| Bereza (III) | 0–4 | Minsk (II) |
| Chaussy (A) | 0–8 | Belshina Bobruisk (II) |
| Vertikal Kalinkovichi (III) | 3–1 | DSK Gomel (III) |
Sixteen winners of the First Round were joined by all sixteen teams of the Premier League. The games were played on September 3, 4 and 7, 2008.
| Team 1 | Score | Team 2 |
|---|---|---|
| Zvezda-BGU Minsk (III) | 1–4 | Granit Mikashevichi |
| PMC Postavy (II) | 1–3 | MTZ-RIPO Minsk |
| Lida (II) | 1–1 (aet, p.1–3) | Neman Grodno |
| Vertikal Kalinkovichi (III) | 0–4 | Lokomotiv Minsk |
| Veras Nesvizh (II) | 0–2 | Naftan Novopolotsk |
| Osipovichi (III) | 2–4 (aet) | Shakhtyor Soligorsk |
| Vedrich-97 Rechytsa (II) | 0–1 | Smorgon |
| Dinamo-Belcard Grodno (II) | 0–0 (aet, p.3–2) | Dnepr Mogilev |
| Belshina Bobruisk (II) | 2–0 | Dinamo Minsk |
| Klechesk Kletsk (III) | 0–5 | Vitebsk |
| Volna Pinsk (II) | 3–2 | Dinamo Brest |
| Slavia-Mozyr (II) | 1–3 | Torpedo Zhodino |
| Minsk (II) | 2–0 | Savit Mogilev |
| Khimik Svetlogorsk (II) | 0–2 | Gomel |
| Kommunalnik Slonim (II) | 1–0 | Darida Minsk Raion |
| Neman Mosty (III) | 3–7 | BATE Borisov |
The games were played as two-legged ties. The first legs were played on October 11, 12, 29 and November 4, 2008. The second legs were played on November 2 and 20, 2008.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Shakhtyor Soligorsk | 10–0 | Kommunalnik Slonim (II) | 5–0 | 5–0 |
| Naftan Novopolotsk | 7–0 | Lokomotiv Minsk | 3–0 | 4–0 |
| Vitebsk | 3–2 | Torpedo Zhodino | 0–1 | 3–1 (aet) |
| Dinamo-Belcard Grodno (II) | 1–7 | Neman Grodno | 0–4 | 1–3 |
| Volna Pinsk (II) | 2–6 | Gomel | 0–2 | 2–4 |
| Belshina Bobruisk (II) | 1–5 | Granit Mikashevichi | 1–4 | 0–1 |
| MTZ-RIPO Minsk | 6–2 | Smorgon | 4–0 | 2–2 |
| BATE Borisov | (p) 5–5 | Minsk (II) | 1–4 | 4–1 (aet, p. 4–3) |
The first legs were played on March 15, 2009. The second legs were played on March 21, 2009.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Shakhtyor Soligorsk | 5–0 | Granit Mikashevichi | 2–0 | 3–0 |
| Gomel | 2–2 (a) | Naftan Novopolotsk | 1–2 | 1–0 |
| MTZ-RIPO Minsk | 0–3 | Neman Grodno | 0–0 | 0–3 |
| BATE Borisov | 2–1 | Vitebsk | 1–0 | 1–1 |
The first legs were played on April 9, 2009. The second legs were played on April 22, 2009.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Neman Grodno | 2–3 | Shakhtyor Soligorsk | 1–1 | 1–2 |
| Naftan Novopolotsk | 3–0 | BATE Borisov | 1–0 | 2–0 |
| May 31, 2009 18:00 EET |
Naftan Novopolotsk | 2 – 1 (After extra time) |
Shakhtyor Soligorsk | Dinamo Stadium, Minsk |
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