| 2008-10-18 | Dag and RedvBuryLeague Two · England | 1–3 | League Two · England |
| 2008-10-18 | ArsenalvEvertonPremier League · England | 3–1 | Premier League · England |
| 2008-10-18 | MillwallvLeedsLeague One · England | 3–1 | League One · England |
| 2008-10-18 | XerezvLas PalmasLa Liga 2 · Spain | 1–0 | La Liga 2 · Spain |
| 2008-10-18 | Notts CountyvMacclesfieldLeague Two · England | 1–1 | League Two · England |
| 2008-10-18 | RotherhamvBarnetLeague Two · England | 3–4 | League Two · England |
| 2008-10-18 | FrosinonevRiminiSerie B · Italy | 3–1 | Serie B · Italy |
| 2008-10-18 | WolfsburgvBielefeldBundesliga · Germany | 4–1 | Bundesliga · Germany |
| 2008-10-18 | Raith RvsvAyrLeague One · Scotland | 3–2 | League One · Scotland |
| 2008-10-18 | SouthamptonvWatfordChampionship · England | 0–3 | Championship · England |
| 2008-10-18 | HuddersfieldvBristol RvsLeague One · England | 1–1 | League One · England |
| 2008-10-18 | BresciavTriestinaSerie B · Italy | 3–2 | Serie B · Italy |
| 2008-10-18 | DoncastervBlackpoolChampionship · England | 0–0 | Championship · England |
| 2008-10-18 | Crystal PalacevBarnsleyChampionship · England | 3–0 | Championship · England |
| 2008-10-18 | StranraervQueens ParkLeague One · Scotland | 0–0 | League One · Scotland |
| 2008-10-18 | WalsallvHartlepoolLeague One · England | 2–3 | League One · England |
| 2008-10-18 | DundeevRoss CountyChampionship · Scotland | 1–2 | Championship · Scotland |
| 2008-10-18 | AlavesvMurciaLa Liga 2 · Spain | 4–1 | La Liga 2 · Spain |
| 2008-10-18 | LiverpoolvWiganPremier League · England | 3–2 | Premier League · England |
| 2008-10-18 | StirlingvBrechinLeague One · Scotland | 1–2 | League One · Scotland |
| 2008-10-18 | AlloavArbroathLeague One · Scotland | 2–1 | League One · Scotland |
| 2008-10-18 | PeterheadvEast FifeLeague One · Scotland | 0–1 | League One · Scotland |
| 2008-10-18 | Ath MadridvReal MadridLa Liga · Spain | 1–2 | La Liga · Spain |
| 2008-10-18 | FiorentinavRegginaSerie A · Italy | 3–0 | Serie A · Italy |
| 2008-10-18 | Man UnitedvWest BromPremier League · England | 4–0 | Premier League · England |
| 2008-10-18 | IpswichvSwanseaChampionship · England | 2–2 | Championship · England |
| 2008-10-18 | DunfermlinevPartickChampionship · Scotland | 1–0 | Championship · Scotland |
| 2008-10-18 |  MonacovNiceLigue 1 · France | 1–2 | Ligue 1 · France |
| 2008-10-18 | Aston VillavPortsmouthPremier League · England | 0–0 | Premier League · England |
| 2008-10-18 | PanioniosvArisSuper League · Greece | 2–1 | Super League · Greece |
| 2008-10-18 | OxfordvBurtonNational League · England | 2–1 | National League · England |
| 2008-10-18 | SouthendvSwindonLeague One · England | 2–1 | League One · England |
| 2008-10-18 | SassuolovMantovaSerie B · Italy | 1–2 | Serie B · Italy |
| 2008-10-18 | Inverness CvCelticPremiership · Scotland | 1–2 | Premiership · Scotland |
| 2008-10-18 | TwentevHeraclesEredivisie · Netherlands | 2–0 | Eredivisie · Netherlands |
| 2008-10-18 | GrossetovSalernitanaSerie B · Italy | 6–2 | Serie B · Italy |
| 2008-10-18 | TubizevGentPro League · Belgium | 0–1 | Pro League · Belgium |
| 2008-10-18 | LyonvLilleLigue 1 · France | 2–2 | Ligue 1 · France |
| 2008-10-18 | Leyton OrientvTranmereLeague One · England | 0–1 | League One · England |
| 2008-10-18 | WolvesvCoventryChampionship · England | 2–1 | Championship · England |
| 2008-10-18 | MiddlesbroughvChelseaPremier League · England | 0–5 | Premier League · England |
| 2008-10-18 | Werder BremenvDortmundBundesliga · Germany | 3–3 | Bundesliga · Germany |
| 2008-10-18 | NorthamptonvYeovilLeague One · England | 3–0 | League One · England |
| 2008-10-18 | Sevilla BvZaragozaLa Liga 2 · Spain | 0–4 | La Liga 2 · Spain |
| 2008-10-18 | ShrewsburyvBournemouthLeague Two · England | 4–1 | League Two · England |
| 2008-10-18 | BursasporvEskisehirsporSüper Lig · Turkey | 1–2 | Süper Lig · Turkey |
| 2008-10-18 | CarlislevPeterboroLeague One · England | 3–3 | League One · England |
| 2008-10-18 | CheltenhamvScunthorpeLeague One · England | 1–2 | League One · England |
| 2008-10-18 | HerthavStuttgartBundesliga · Germany | 2–1 | Bundesliga · Germany |
| 2008-10-18 | StandardvBergenPro League · Belgium | 2–1 | Pro League · Belgium |