First Round
The First Round consisted of 32 teams from lower Icelandic divisions. The matches were played between May 24 and 27, 2008.
| Team 1 | Score | Team 2 |
|---|---|---|
| Höfrungur | 0–4 | Skallagrímur |
| Garðabæjar | 0–1 | Augnablik |
| UMF Snæfell | 0–3 | UMF Grundarfjarðar |
| Völsungur | 1–3 | Magni |
| UMF Tindastóll | 2–1 | Kormáks |
| Vesturbæjar | 3–4 | Ýmir |
| Þróttur Vogum | 3–1 | UMF Gnúpverja |
| Ægir | 1–2 | Elliði |
| Reyðarfjörður | 4–3 | Boltafélag Norðfjarðar |
| UMF Hrunamanna | 0–4 | Árborgar |
| Berserkir | 3–0 | UMF Kjalnesinga |
| Leiknir Fáskrúðsfirði | 1–3 | Spyrnir |
| Hvíti riddarinn | 3–2 (aet) | UMF Laugdæla |
| UMF Álftanes | 1–3 | Hamrarnir/Vinir |
| Rangæinga | 2–4 | Breiðholts |
| Dalvík/Reynir | 0–1 | UMF Hvöt |
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