The 2008-09 Libyan Cup is the 19th edition of the competition since its inception in 1976.
45 teams will be entering the competition, composed of 5 sides from the Libyan Third Division, and 40 sides from the Libyan Second Division. 26 were drawn into the First Round, while the other 18 were automatically drawn into the Second Round. The sides participating in the First Round were drawn into regional groups. The Second Round will consist of 32 sides, 18 in the Eastern Section, and 14 in the Western Section. 16 sides from the Second Round will go through to the Round of 32, where they will be joined by the 16 sides in the Libyan Premier League. All ties this season will be one-off ties, compared to previous seasons, where the later rounds were two-legged affairs.
If any of the matches end in a draw, then the tie(s) will be settled by a penalty shootout. [1] This stands until the semi-final stage, where the tie(s) will be settled by two 15-minute halves of extra time, then followed by a penalty shootout if the scores remain level. [1]
The draw was made on March 26, 2009 at 22:00 EET. Matches will be settled by a penalty shootout immediately after the match should a tie end in a draw. [2] The stadia were selected by the Libyan Football Federation. The ties will be played between May 1, 2009 and May 6, 2009. If ties are won by the team playing at home, then this team will play away from home against their next opponents in the Round of 16. [3]
| Tie no | Home team | Score | Away team | Stadium |
|---|---|---|---|---|
| 1 | Hilal Benghazi | 3 – 1 | Al Anwaar | Martyrs of February Stadium |
| 2 | Ahly Benghazi | 4 – 2 | Tahaddy | Martyrs of February Stadium |
| 3 | Al Qal'aa | 0 – 0 | Jazeera | 2 March Stadium |
| Jazeera won 4 - 2 on penalties | ||||
| 4 | Darnes | 0 – 1 | Madina | Derna Stadium |
| 5 | Khaleej Sirte | 2 – 0 | Abi al Ashar | 2 March Stadium |
| 6 | Nasr | 0 – 0 | Nojom Ajdabiya | Martyrs of February Stadium |
| Nojom Ajdabiya won 5 - 4 on penalties | ||||
| 7 | Ittihad Gheryan | 0 – 2 | Sweahly | GMR Stadium |
| 8 | Wahda Tripoli | 1 – 1 | Wahda Benghazi | GMR Stadium |
| Wahda Tripoli won 4 - 2 on penalties | ||||
| 9 | Shamaal Benghazi | 0 – 4 | Tersanah | Martyrs of February Stadium |
| 10 | Nojom Al Baazah | 1 – 4 | Akhdar | 9 July Stadium |
| 11 | Al Mukhtar Tobruk | 0 – 2 | Ahly Tripoli | Derna Stadium |
| 12 | Wefaq Sabratha | 1 – 0 | Dhahra | Sabratha Stadium |
| 13 | Ittihad Tripoli | 5 – 0 | Shabaab al Jabal | 11 June Stadium |
| 14 | Aman al Aam | 1 – 1 | Al Mahdeeya | GMR Stadium |
| Mahdeeya won 3 - 2 on penalties | ||||
| 15 | Shat | 7 – 0 | Hilal Tobruk | GMR Stadium |
| 16 | Olomby | 3 – 1 | Yarmouk | Zaawia Stadium |
The draw was made on May 23, 2009 at 22:00 EET. Matches will be settled by a penalty shootout immediately after the match should a tie end in a draw. The stadia were selected by the Libyan Football Federation. [4]
Ties to be played week commencing May 31, 2009 [5]
| Tie no | Home team | Score | Away team | Stadium |
|---|---|---|---|---|
| 1 | Jazeera | 2 – 1 | Wefaq Sabratha | GMR Stadium |
| 2 | Al Sweahly | 1 – 3 | Ittihad Tripoli | 9 July Stadium |
| 3 | Wahda Tripoli | 0 – 2 | Hilal Benghazi | GMR Stadium |
| 4 | Tersanah | 0 – 0 | Olomby | GMR Stadium |
| Tersanah won 3 - 1 on penalties | ||||
| 5 | Akhdar | 2 – 0 | Ahly Benghazi | Al Bayda Stadium |
| 6 | Madina | 3 – 0 | Khaleej Sirte | 11 June Stadium |
| 7 | Ahly Tripoli | 2 – 0 | Nojom Ajdabiya | 11 June Stadium |
| 8 | Mahdeeya | 2 – 2 | Shat | Sabha Stadium |
| Shat won 5 - 4 on penalties | ||||
The draw was made on June 22, 2009 at the LFF headquarters in Tripoli. [6] The ties will be played over three days commencing June 30, 2009.
| Tie no | Home team | Score | Away team | Stadium |
|---|---|---|---|---|
| 1 | Ahly Tripoli | 4 – 1 | Jazeera | 11 June Stadium |
| 2 | Madina | 0 – 0 | Tersanah | 11 June Stadium |
| Tersanah won 5 - 4 on penalties | ||||
| 3 | Hilal | 2 – 1 | Akhdar | Martyrs of February Stadium |
| 4 | Al-Ittihad | 7 – 1 | Shat | 11 June Stadium |
| Hilal | 2 – 1 | Akhdar |
|---|---|---|
Tariq al Aqrabi  39'Naaji al Maqrahi 68' | Wisaam Boukteaf 90+5' |
The draw was made on June 30. The ties will be played over July 5 and July 6. [7]
| Tie no | Home team | Score | Away team | Stadium |
|---|---|---|---|---|
| 1 | Tersanah | 2 – 2 | Hilal | GMR Stadium |
| Tersanah won 3 – 1 on penalties | ||||
| 2 | Ahly Tripoli | 0 – 0 | Al-Ittihad | 11 June Stadium |
| Ittihad won 5 – 4 on penalties | ||||
| Tersanah | 2 – 2 | Hilal |
|---|---|---|
| Samir Al Wahaj 5', 60' (pen.) | Tariq al Aqrabi 27' Hamid al Tayeb 44' |
| Al-Ittihad | 2 – 2 (a.e.t.) | Tersanah |
|---|---|---|
| Ahmed Zuway 38', 107' | (Report) | Samir Al Wahaj 27', 91' |
| Penalties | ||
Shaban  Za'abia  Rahuma Pierre Koulibaly | 3 – 2 Tersanah went first | Ambaya Jamil Qasim Falicko al Boudy |
Essam Abd El Fatah 
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