2008–09 UEFA Cup first round
The first round of the 2008–09 UEFA Cup began on 16 September 2008, which narrowed clubs down to 40 teams in preparation for the group stage.
Seeding
    
Summary
    
First leg
    
| Hertha BSC  | 2–0 |  St Patrick's Athletic | 
|---|---|---|
| Nicu  50' Cícero  77' | Report | 
| APOEL  | 1–4 |  Schalke 04 | 
|---|---|---|
| Mirosavljević  72' | Report | Westermann  25' Rakitić  36' Sánchez  41' Altıntop  88' | 
| Nordsjælland  | 0–2 |  Olympiacos | 
|---|---|---|
| Report | Mitroglou  74' Leto  90+1' | 
| Slaven Belupo  | 1–2 |  CSKA Moscow | 
|---|---|---|
| Jurić  43' | Report | Vágner Love  81', 89' (pen.) | 
| Brøndby  | 1–2 |  Rosenborg | 
|---|---|---|
| Krohn-Dehli  63' | Sapara  29' Skjelbred  55' | 
| Cherno More  | 1–2 |  Stuttgart | 
|---|---|---|
| Dyakov  42' | Report | Gómez  66', 81' | 
| Borac Čačak .svg.png.webp) | 1–4 |  Ajax | 
|---|---|---|
| Milovanović  50' | Report | Sulejmani  11' Suárez  35' Huntelaar  71', 86' | 
| Tottenham Hotspur  | 2–1 |  Wisła Kraków | 
|---|---|---|
| Bentley  33' Bent  73' | Report | Jirsák  34' | 
| FC Moscow  | 1–2 |  Copenhagen | 
|---|---|---|
| Samedov  90+1' | Report | Nordstrand  45' (pen.) Sionko  90+3' | 
| MŠK Žilina  | 1–1 |  Levski Sofia | 
|---|---|---|
| Vladavić  49' (pen.) | Report | Joãozinho  64' | 
| Borussia Dortmund  | 0–2 |  Udinese | 
|---|---|---|
| Report | Floro Flores  8' Inler  34' | 
| Hapoel Tel Aviv  | 1–2 |  Saint-Étienne | 
|---|---|---|
| Lala  88' | Report | Payet  7' Feindouno  60' | 
| Litex Lovech  | 1–3 |  Aston Villa | 
|---|---|---|
| Popov  10' | Report | Reo-Coker  45+1' Barry  72' (pen.) Petrov  90+2' | 
| Austria Wien  | 2–1 |  Lech Poznań | 
|---|---|---|
| Schiemer  64', 76' | Report | Rengifo  65' | 
| Vitória de Setúbal  | 1–1 |  Heerenveen | 
|---|---|---|
| Leandro Carrijo  67' | Report | Elyounoussi  90' | 
| Baník Ostrava  | 0–1 |  Spartak Moscow | 
|---|---|---|
| Report | Fathi  56' | 
| Beşiktaş  | 1–0 |  Metalist Kharkiv | 
|---|---|---|
| Hološko  51' | Report | Report | 
| Portsmouth  | 2–0 |  Vitória de Guimarães | 
|---|---|---|
| Diarra  39' Defoe  60' | Report | 
| Kayserispor  | 1–2 |  Paris Saint-Germain | 
|---|---|---|
| Toledo  87' | Report | Kežman  5' Luyindula  89' | 
| Sevilla  | 2–0 |  Red Bull Salzburg | 
|---|---|---|
| Capel  6' Adriano  90+2' | Report | 
| Wolfsburg  | 1–0 |  Rapid București | 
|---|---|---|
| Grafite  47' (pen.) | Report | 
| Omonia  | 1–2 |  Manchester City | 
|---|---|---|
| Duro  49' | Report | Jô  59', 72' | 
| Young Boys  | 2–2 | .svg.png.webp) Club Brugge | 
|---|---|---|
| Schneuwly  16' Doumbia  87' | Report | Sonck  36' Clement  73' | 
| Nancy  | 1–0 |  Motherwell | 
|---|---|---|
| Berenguer  42' | Report | 
| Bellinzona  | 3–4 |  Galatasaray | 
|---|---|---|
| Lustrinelli  32' Sermeter  47' La Rocca  90' | Report | Kewell  39' Baroš  61', 81' Lincoln  90+5' | 
| N.E.C.  | 1–0 |  Dinamo București | 
|---|---|---|
| Van Beukering  57' | Report | 
| Racing Santander  | 1–0 |  Honka | 
|---|---|---|
| Pereira  57' | Report | 
Second leg
    
Hertha BSC won 2–0 on aggregate.
| Schalke 04  | 1–1 |  APOEL | 
|---|---|---|
| Pander  58' | Report | Pinto  6' | 
Schalke 04 won 5–2 on aggregate.
| Olympiacos  | 5–0 |  Nordsjælland | 
|---|---|---|
| Torosidis  11' Diogo  30', 43' Kovačević  72', 80' | Report | 
Olympiacos won 7–0 on aggregate.
| CSKA Moscow  | 1–0 |  Slaven Belupo | 
|---|---|---|
| A. Berezutski  37' | Report | 
CSKA Moscow won 3–1 on aggregate.
| Rosenborg  | 3–2 |  Brøndby | 
|---|---|---|
| Ya Konan  15' Skjelbred  74' Sapara  87' (pen.) | Report | M. Rasmussen  26' Kristiansen  36' | 
Rosenborg won 5–3 on aggregate.
| Stuttgart  | 2–2 |  Cherno More | 
|---|---|---|
| Hitzlsperger  83' Gómez  90+3' | report | Yurukov  48' Iliev  79' | 
Stuttgart won 4–3 on aggregate.
Rennes 2–2 Twente on aggregate. Twente won on away goals.
| Ajax  | 2–0 | .svg.png.webp) Borac Čačak | 
|---|---|---|
| Sarpong  71' Suárez  90+5' | Report | 
Ajax won 6–1 on aggregate.
| Wisła Kraków  | 1–1 |  Tottenham Hotspur | 
|---|---|---|
| Brożek  83' | Report | Głowacki  58' (o.g.) | 
Tottenham Hotspur won 3–2 on aggregate.
| Copenhagen  | 1–1 |  FC Moscow | 
|---|---|---|
| Sheshukov  54' (o.g.) | Report | Bracamonte  37' | 
Copenhagen won 3–2 on aggregate.
| Levski Sofia  | 0–1 |  MŠK Žilina | 
|---|---|---|
| Report | Adauto  61' | 
MŠK Žilina won 2–1 on aggregate.
| Udinese  | 0–2 (a.e.t.) |  Borussia Dortmund | 
|---|---|---|
| Report | Hajnal  45+1', 90+2' | |
| Penalties | ||
| Domizzi  Quagliarella  Pepe  Inler  Luković  | 4–3 |  Hajnal  Şahin  Kehl  Błaszczykowski  Valdez | 
Borussia Dortmund 2–2 Udinese on aggregate. Udinese won 4–3 on penalties.
| Artmedia Bratislava  | 0–2 |  Braga | 
|---|---|---|
| Report | Aguiar  11' (pen.), 31' | 
Braga won 6–0 on aggregate.
Feyenoord 2–2 Kalmar on aggregate. Feyenoord won on away goals.
| Unirea Urziceni  | 0–2 |  Hamburg | 
|---|---|---|
| Report | Petrić  27', 51' | 
Hamburg won 2–0 on aggregate.
| Saint-Étienne  | 2–1 |  Hapoel Tel Aviv | 
|---|---|---|
| Gomis  25', 76' | Report | Yeboah  90+1' | 
Saint-Étienne won 4–2 on aggregate.
| Zürich  | 0–1 |  Milan | 
|---|---|---|
| Report | Shevchenko  70' | 
Milan won 4–1 on aggregate.
| Partizan .svg.png.webp) | 1–0 |  Timișoara | 
|---|---|---|
| Stevanović  70' | Report | 
Partizan won 3–1 on aggregate.
| Aston Villa  | 1–1 |  Litex Lovech | 
|---|---|---|
| Harewood  27' | Report | Niflore  53' (pen.) | 
Aston Villa won 4–2 on aggregate.
| Lech Poznań  | 4–2 (a.e.t.) |  Austria Wien | 
|---|---|---|
| Rengifo  10' Peszko  85' Lewandowski  99' Murawski  120+1' | Report | Ačimovič  63' (pen.) Hattenberger  100' | 
Lech Poznań won 5–4 on aggregate.
| Heerenveen  | 5–2 |  Vitória de Setúbal | 
|---|---|---|
| Paulo Henrique  4' Sibon  11', 24' Elyounoussi  50', 68' | Report | Gama  57' Chaves  63' | 
Heerenveen won 6–3 on aggregate.
| Deportivo La Coruña  | 2–0 (a.e.t.) |  Brann | 
|---|---|---|
| Colotto  18', 76' | Report | |
| Penalties | ||
| Sergio  Mista  Guardado  Verdú  | 3–2 |  Bjarnson  Vaagan Moen  Bakke  Austin  Hanstveit | 
Brann 2–2 Deportivo La Coruña on aggregate. Deportivo La Coruña won 3–2 on penalties.
| Vaslui  | 1–1 |  Slavia Prague | 
|---|---|---|
| Burdujan  21' | Report | Brabec  48' | 
Slavia Prague 1–1 Vaslui on aggregate. Slavia Prague won on away goals.
| Spartak Moscow  | 1–1 |  Baník Ostrava | 
|---|---|---|
| Bazhenov  3' | Report | Otepka  32' | 
Spartak Moscow won 2–1 on aggregate.
| Metalist Kharkiv  | 4–1 |  Beşiktaş | 
|---|---|---|
| Jajá  20', 74' Dević  30' Gancarczyk  79' | Report | Nobre  90' | 
Metalist Kharkiv won 4–2 on aggregate.
| Vitória de Guimarães  | 2–2 (a.e.t.) |  Portsmouth | 
|---|---|---|
| Douglas  19' Alves  32' | Report | Crouch  105', 111' | 
Portsmouth won 4–2 on aggregate.
Paris Saint-Germain won 2–1 on aggregate.
| Red Bull Salzburg  | 0–2 |  Sevilla | 
|---|---|---|
| Report | Kanouté  38', 57' (pen.) | 
Sevilla won 4–0 on aggregate.
| Rapid București  | 1–1 |  Wolfsburg | 
|---|---|---|
| Maftei  70' | Report | Grafite  15' | 
Wolfsburg won 2–1 on aggregate.
Sampdoria won 7–1 on aggregate.
Valencia won 3–1 on aggregate.
| Sparta Prague  | 3–3 |  Dinamo Zagreb | 
|---|---|---|
| Kulič  19' Kladrubský  23', 82' (pen.) | Report | Morales  17' Lovren  30' Badelj  65' | 
Dinamo Zagreb 3–3 Sparta Prague on aggregate. Dinamo Zagreb won on away goals.
| Manchester City  | 2–1 |  Omonia | 
|---|---|---|
| Elano  48' Wright-Phillips  55' | Report | Alabi  78' | 
Manchester City won 4–2 on aggregate.
| Club Brugge .svg.png.webp) | 2–0 |  Young Boys | 
|---|---|---|
| Akpala  17' Sonck  29' | Report | 
Club Brugge won 4–2 on aggregate.
| Motherwell  | 0–2 |  Nancy | 
|---|---|---|
| Report | Fortuné  18' Gavanon  23' | 
Nancy won 3–0 on aggregate.
Standard Liège won 4–3 on aggregate.
| Benfica  | 2–0 |  Napoli | 
|---|---|---|
| Reyes  57' Nuno Gomes  84' | Report | 
Benfica won 4–3 on aggregate.
| Galatasaray  | 2–1 |  Bellinzona | 
|---|---|---|
| Baroš  24' (pen.) Yıldız  86' | Sermeter  52' (pen.) | 
Galatasaray won 6–4 on aggregate.
NEC won 1–0 on aggregate.
| Honka  | 0–1 |  Racing Santander | 
|---|---|---|
| Report | Bedia  4' | 
Racing Santander won 2–0 on aggregate.

