| 2008-09-20 | Port ValevMacclesfieldLeague Two · England | 1–4 | League Two · England |
| 2008-09-20 | AnconavPiacenzaSerie B · Italy | 0–1 | Serie B · Italy |
| 2008-09-20 | Schalke 04vEin FrankfurtBundesliga · Germany | 1–0 | Bundesliga · Germany |
| 2008-09-20 | CataniavAtalantaSerie A · Italy | 1–0 | Serie A · Italy |
| 2008-09-20 | BrightonvWalsallLeague One · England | 0–1 | League One · England |
| 2008-09-20 | AlloavEast FifeLeague One · Scotland | 0–3 | League One · Scotland |
| 2008-09-20 | CarlislevLeedsLeague One · England | 0–2 | League One · England |
| 2008-09-20 | LivornovPisaSerie B · Italy | 1–1 | Serie B · Italy |
| 2008-09-20 | DunfermlinevRoss CountyChampionship · Scotland | 3–1 | Championship · Scotland |
| 2008-09-20 | LillevAuxerreLigue 1 · France | 3–2 | Ligue 1 · France |
| 2008-09-20 | BradfordvBournemouthLeague Two · England | 1–3 | League Two · England |
| 2008-09-20 | HamiltonvHibernianPremiership · Scotland | 0–1 | Premiership · Scotland |
| 2008-09-20 | Bayern MunichvWerder BremenBundesliga · Germany | 2–5 | Bundesliga · Germany |
| 2008-09-20 | GraysvWrexhamNational League · England | 2–1 | National League · England |
| 2008-09-20 | VicenzavBariSerie B · Italy | 1–2 | Serie B · Italy |
| 2008-09-20 | AnkaragucuvBuyuksehyrSüper Lig · Turkey | 0–0 | Süper Lig · Turkey |
| 2008-09-20 | Forest GreenvStevenageNational League · England | 0–3 | National League · England |
| 2008-09-20 | MontrosevEast StirlingLeague Two · Scotland | 3–0 | League Two · Scotland |
| 2008-09-20 | RiminivEmpoliSerie B · Italy | 0–1 | Serie B · Italy |
| 2008-09-20 | HartlepoolvOldhamLeague One · England | 3–3 | League One · England |
| 2008-09-20 | GrenoblevBordeauxLigue 1 · France | 0–1 | Ligue 1 · France |
| 2008-09-20 | OxfordvCrawley TownNational League · England | 1–2 | National League · England |
| 2008-09-20 | LarisavXanthiSuper League · Greece | 0–1 | Super League · Greece |
| 2008-09-20 | DumbartonvCowdenbeathLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-09-20 | TriestinavSassuoloSerie B · Italy | 1–1 | Serie B · Italy |
| 2008-09-20 | AltrinchamvLewesNational League · England | 1–0 | National League · England |
| 2008-09-20 | TorquayvEastbourne BoroughNational League · England | 2–0 | National League · England |
| 2008-09-20 | Raith RvsvStirlingLeague One · Scotland | 1–1 | League One · Scotland |
| 2008-09-20 | PanthrakikosvPAOKSuper League · Greece | 0–1 | Super League · Greece |
| 2008-09-20 | BlackburnvFulhamPremier League · England | 1–0 | Premier League · England |
| 2008-09-20 | StockportvSwindonLeague One · England | 1–1 | League One · England |
| 2008-09-20 | ColchestervMilton Keynes DonsLeague One · England | 0–3 | League One · England |
| 2008-09-20 | YorkvSalisburyNational League · England | 1–1 | National League · England |
| 2008-09-20 | MillwallvCheltenhamLeague One · England | 2–0 | League One · England |
| 2008-09-20 | FenerbahcevGenclerbirligiSüper Lig · Turkey | 3–0 | Süper Lig · Turkey |
| 2008-09-20 | RotherhamvLutonLeague Two · England | 1–0 | League Two · England |
| 2008-09-20 | AlbinoleffevAvellinoSerie B · Italy | 2–1 | Serie B · Italy |
| 2008-09-20 | PartickvMortonChampionship · Scotland | 2–1 | Championship · Scotland |
| 2008-09-20 | MansfieldvCambridgeNational League · England | 1–1 | National League · England |
| 2008-09-20 | AlavesvLevanteLa Liga 2 · Spain | 2–2 | La Liga 2 · Spain |
| 2008-09-20 | ArisvPanathinaikosSuper League · Greece | 1–2 | Super League · Greece |
| 2008-09-20 | PeterborovTranmereLeague One · England | 2–2 | League One · England |
| 2008-09-20 | EskisehirsporvSivassporSüper Lig · Turkey | 2–2 | Süper Lig · Turkey |
| 2008-09-20 | Airdrie UtdvClydeChampionship · Scotland | 0–2 | Championship · Scotland |
| 2008-09-20 | Le HavrevLyonLigue 1 · France | 0–1 | Ligue 1 · France |
| 2008-09-20 | HuddersfieldvNorthamptonLeague One · England | 3–2 | League One · England |
| 2008-09-20 | ArbroathvQueens ParkLeague One · Scotland | 1–1 | League One · Scotland |
| 2008-09-20 | HistonvNorthwichNational League · England | 2–1 | National League · England |
| 2008-09-20 | Nott'm ForestvCharltonChampionship · England | 0–0 | Championship · England |
| 2008-09-20 | HerefordvScunthorpeLeague One · England | 1–2 | League One · England |