Libyan Cup 2008–09 – Round of 16
# Libyan Cup 2008–09 – Round of 16

## Draw

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.

Ties to be played week commencing May 31, 2009

| 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 |||||

## Fixtures and results

Fixtures announced on May 24, 2009 Division of each club in parentheses

$^1$ Zidane's goal was timed at 20 seconds.

