The draw for the Round of 16 of the 2009–10 Libyan Cup was made on January 28, 2010 at 21:30 EET. The dates and times for the 8 ties were confirmed on January 31.[1] Ties are to be played over the period February 7–February 9, 2010. If any of the ties end in a draw after 90 minutes, then the tie goes immediately to a penalty shootout.
All times local (EET)
| February 7, 2010 | Wefaq Sabratah | 0 – 0 (3 – 2 pens.) |
Rafiq Sorman | Sabratha | ||
| 15:00 | Stadium: Sabratah Stadium |
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| February 7, 2010 | Ahly Tripoli | 1 – 0 | Shat | Tripoli | ||
| 17:00 | Mohammad al Maghrabi 84' | Stadium: 11 June Stadium |
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| February 8, 2010 | Nasr | 1 – 0 | Khaleej Sirte | Benina | ||
| 15:00 | Ndubuisi Eze 59' (pen.) Ibrahim al Haasi 76' |
Maher al Naili 88' | Stadium: Martyrs of February Stadium |
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| February 8, 2010 | Aman al Aam | 0 – 1 | Tahaddy | Tripoli | ||
| 17:00 | Solomonson Ezékoka 45+1' 86' | Stadium: GMR Stadium |
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| February 8, 2010 | Ittihad | 1 – 0 | Mahalla | Tripoli | ||
| 17:00 | Ahmed Abdulkafi 66' | Stadium: 11 June Stadium |
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| February 9, 2010 | Hiyad | 2 – 2 (5 – 3 pens.) |
Suqoor | Misrata | ||
| 15:00 | Alpha Barry 40', 67' | Mohammad Hadoud 38' Salem Bazeen 90' |
Stadium: 9 July Stadium |
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| February 9, 2010 | Benghazi al Jadeeda | 1 – 0 | Sharrara | Benina | ||
| 15:00 | 85' | Stadium: Martyrs of February Stadium |
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| February 23, 2010 | Madina | 3 – 1 | Akhdar | Tripoli | ||
| 16:00 | Stefan de Paul 44' (pen.) Mohammad Mqarej 68' Abdallah Sharif 82' Ismael Bangoura 55' Ayman Khalifi 73' |
Abdelhameed Zidane 21' Hishaam Lahmar 66' |
Stadium: 11 June Stadium |
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