All times given as local time (UTC+2)

Libyan Cup 2008–09: 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.

Eastern Section

This group will contain 18 sides, 7 of which had qualified from groups A & B in the first round. Over the 9 matches, nine will qualify for the Round of 32.

Al Taw'eah0 – 5Shabab al Jabal
10 June Stadium
Referee: Rafa' Zayed
Al Baranes1 – 1
(5 – 4 pen.)		Shamal Benghazi
Referee: Ibrahim al Fakhiry
Al Anwaar2 – 1Al Ansaar
Al Abyaar Stadium
Referee: Ahmed al Jroushi
Al Mukhtar Tobruk1 – 1
(4 – 3 pen.)		Benghazi al Jadeeda
1H' 2H' (pen.)
Referee: Abdallah Fdhail
Darnes1 – 0Al Sawaed
Referee: Anwar Abdesalam
Al Wahda B.2 – 0Al Najma
Referee: Nabeel al Kawaash
Wefaq Ajdabiya1 – 3Al Tahaddi
2H' GhanaMousa Malik 18' 30'
Osama al Qataani soccer ball with red X 40'
2H'
10 June Stadium
Referee: Mohammad al Shelmani
Al Hilal T.1 – 1
(5 – 4 pen.)		Al Hurriya
Referee: Al Taher Fraj
Nojom Ajdabiya2 – 0Al Andalus
10 June Stadium
Referee: Mohammad al Jilaly

Western Section

This group will contain 14 sides, 6 of which had qualified from Groups C & D in the first round. Over the 7 ties, 7 teams will go through to the Round of 32.

Al Jamarek1 – 2Al Mahdeeya
Al Hiyad0 – 1Abi al Ashar
89'
Al Yarmouk2 – 1Rafik Sorman
Ashraf Boukrash pen.'
Ahmad al Danqaawi
Nojoom Al Baazah0 – 2Al Tala'e
Baazah Stadium
Al Majd1 – 2Al Ittihad Gheryan
Al Dhahra Tripoli1 – 1 (4 - 3 pens)Al Mahalla
Al Faaluja1 – 2Al Qal'aa
soccer ball with red X Abdelrahman al Kaadouaa 1H' (pen.)
Ibrahim al Maghrabi 1H'
Nizaar Qaanoon Red card 2H'
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