The first round of the 2008–09 UEFA Cup was played from 16 September to 2 October 2008, which narrowed clubs down to 40 teams in preparation for the group stage.
[1] Times are CEST (UTC+2), as listed by UEFA.
[4] The draw was based on their coefficient ranking with one exception: no country can have multiple teams in any group.
The draw, which was conducted by UEFA General Secretary David Taylor, was held on 29 August 2008 at 13:00 CET in Monaco.
The matches were played on 18 September and 2 October 2008.
Nine of the 40 ties were won by the unseeded team.
The nine seeded losing teams, with their ranking, were: Everton (50), Rapid București (58), Beşiktaş (60), Sparta Prague (68), Dinamo București (69), Levski Sofia (80), Austria Wien (82), Rennes (97) and Hapoel Tel Aviv (108).
2–2 on aggregate; Deportivo La Coruña won 3–2 on penalties.
1–1 on aggregate; Slavia Prague won on away goals.
3–3 on aggregate; Dinamo Zagreb won on away goals.