| 1 | Luka Modrić | Dinamo Zagreb | Tottenham Hotspur Football Club | €22.5M | 1 July 2008 |
| 2 | Hulk | Tokyo Verdy | Futebol Clube do Porto | €19M | 25 July 2008 |
| 3 | James Milner | Newcastle United Football Club | Aston Villa Football Club | €15M | 29 August 2008 |
| 4 | Thiago Silva | Fluminense | Associazione Calcio Milan | €10M | 1 January 2009 |
| 5 | Hugo Lloris | Olympique Gymnaste Club Nice Côte d'Azur | Olympique Lyonnais | €8.5M | 1 July 2008 |
| 6 | Stevan Jovetic | FK Partizan | Associazione Calcio Fiorentina | €8M | 1 July 2008 |
| 7 | Miralem Pjanić | Football Club de Metz | Olympique Lyonnais | €7.5M | 1 July 2008 |
| 8 | Zoran Tosic | FK Partizan | Manchester United Football Club | €7M | 1 January 2009 |
| 9 | Hugo Rodallega | Impulsora del Deportivo Necaxa S.A. de C.V. | WIG | €4.8M | 26 January 2009 |
| 10 | Scott Carson | Liverpool Football Club | West Brom | €4M | 18 July 2008 |
| 11 | Simon Kjær | FC Midtjylland | Palermo FC | €4M | 1 July 2008 |
| 12 | Steven Davis | Fulham Football Club | Rangers Football Club | €3.8M | 1 August 2008 |
| 13 | Sokratis Papastathopoulos | AEK Athens FC | Genoa Cricket and Football Club | €3.8M | 1 August 2008 |
| 14 | Philippe Coutinho | — | Inter | €3.8M | 23 July 2008 |
| 15 | Hugo Rodallega | Club de Fútbol Monterrey Rayados A.C. | Impulsora del Deportivo Necaxa S.A. de C.V. | €3.5M | 1 July 2008 |
| 16 | Kévin Gameiro | Racing Club de Strasbourg Alsace | Football Club Lorient-Bretagne Sud | €3M | 1 July 2008 |
| 17 | Antonio Mirante | Juventus Football Club | Sampdoria | €2.7M | 1 July 2008 |
| 18 | Darwin Quintero | Deportivo Pereira | Club Santos Laguna S. A. de C. V. | €2.5M | 1 January 2009 |
| 19 | Dante | Royal Standard Club de Liège | Borussia Mönchengladbach | €2.5M | 1 January 2009 |
| 20 | Steve Mandanda | Le Havre Athletic Club | Olympique de Marseille | €2.5M | 1 July 2008 |
| 21 | Nordin Amrabat | VVV-Venlo | Eindhovense Voetbalvereniging Philips Sport Vereniging | €2.3M | 1 July 2008 |
| 22 | Lazaros Christodoulopoulos | PAOK | Panathinaikos Athlitikos Omilos | €2.2M | 1 July 2008 |
| 23 | David Ospina | Atletico Nacional | Olympique Gymnaste Club Nice Côte d'Azur | €2M | 9 July 2008 |
| 24 | Maxi Moralez | — | Club Atlético Vélez Sársfield | €1.9M | 12 January 2009 |
| 25 | Papu Gómez | — | Club Atlético San Lorenzo de Almagro | €1.6M | 29 January 2009 |
| 26 | Christian Eriksen | — | — | €1.5M | 1 January 2009 |
| 27 | Morgan Schneiderlin | Racing Club de Strasbourg Alsace | Southampton FC | €1.5M | 1 July 2008 |
| 28 | Riccardo Saponara | — | — | €1.4M | 1 January 2009 |
| 29 | Ignasi Miquel | — | — | €1.3M | 1 July 2008 |
| 30 | José Callejón | — | Reial Club Deportiu Espanyol de Barcelona S.A.D. | €1.2M | 1 July 2008 |
| 31 | Denys Oliynyk | Dynamo Kyiv | Metalist Kharkiv (- 2016) | €1.2M | 1 January 2009 |
| 32 | Francis Coquelin | — | — | €1M | 1 July 2008 |
| 33 | İlkay Gündoğan | — | 1. FC Nürnberg | €850k | 3 February 2009 |
| 34 | Peter Pekarík | — | VfL Wolfsburg | €850k | 1 January 2009 |
| 35 | Jo Inge Berget | — | — | €650k | 1 August 2008 |
| 36 | Mário Fernandes | — | Grêmio | €450k | 1 March 2009 |
| 37 | Mikhail Sivakov | — | Cagliari Calcio | €450k | 31 January 2009 |
| 38 | Darwin Quintero | Krylia Sovetov | Deportivo Pereira | €450k | 1 July 2008 |
| 39 | Victor Pálsson | Aarhus Gymnastik Forening | — | €400k | 2 January 2009 |
| 40 | Artur Yusupov | — | — | €400k | 1 January 2009 |
| 41 | Massimo Coda | — | Bologna Football Club 1909 | €400k | 1 July 2008 |
| 42 | Robert Lewandowski | — | Lech Poznan | €380k | 1 July 2008 |
| 43 | Lasse Schöne | De Graafschap Doetinchem | Nijmegen Eendracht Combinatie | €360k | 1 July 2008 |
| 44 | Bas Dost | FC Emmen | Heracles Almelo | €300k | 1 July 2008 |
| 45 | Mattia Perin | — | — | €300k | 1 July 2008 |
| 46 | Ritchie De Laet | Stoke City | Manchester United Football Club | €250k | 8 January 2009 |
| 47 | Péter Gulácsi | — | Liverpool Football Club | €250k | 1 September 2008 |
| 48 | Aron Gunnarsson | — | — | €250k | 1 July 2008 |
| 49 | Benjamin Siegrist | — | — | €180k | 1 January 2009 |
| 50 | Duje Cop | HNK Hajduk Split | Nacional | €180k | 1 July 2008 |