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]
See main article: Libyan Cup 2008–09 – first round.
16 sides from the 16 matches being played in this round will go through to the Round of 32, where they will be joined by the 16 Libyan Premier League teams.
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The dates, times, and stadia were announced by the Libyan Football Federation on April 28, 2009.[2]
Division of each club in parentheses
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Fixtures announced on May 24, 2009[3]
Division of each club in parentheses
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1 Zidane's goal was timed at 20 seconds.
The draw was made on June 22, 2009 at the LFF headquarters in Tripoli.[4] 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 | |
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The draw was made on June 30. The ties will be played over July 5 and July 6.[5]
| 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 | |||||
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