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| 11.05.1999 (18) | ![Kozakken Boys Kozakken Boys](https://tmssl.akamaized.net/images/wappen/verysmall/12285.png?lm=1584263669) | 50 Tsd. € |
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| 06.07.1999 (17) | ![FC Dordrecht FC Dordrecht](https://tmssl.akamaized.net/images/wappen/verysmall/1455.png?lm=1690016096) | - |
- |
| 19.05.1999 (18) | ![SV Valkenswaard SV Valkenswaard](https://tmssl.akamaized.net/images/wappen/verysmall/45957.png?lm=1570546729) | - |
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| 12.03.1999 (18) | ![HVC '10 HVC '10](https://tmssl.akamaized.net/images/wappen/verysmall/59328.png?lm=1498568243) | - |
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| 05.03.1999 (18) | ![PSV Eindhoven PSV Eindhoven](https://tmssl.akamaized.net/images/wappen/verysmall/383.png?lm=1682925949) | 75 Tsd. € |
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| 07.10.1999 (17) | ![Fenerbahce Fenerbahce](https://tmssl.akamaized.net/images/wappen/verysmall/36.png?lm=1406739123) | 1,25 Mio. € |
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| 17.08.1999 (17) | ![Manchester United Manchester United](https://tmssl.akamaized.net/images/wappen/verysmall/985.png?lm=1457975903) | - |
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| 21.04.1999 (18) | ![Moreirense FC Moreirense FC](https://tmssl.akamaized.net/images/wappen/verysmall/979.png?lm=1552324606) | - |
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| 30.12.1999 (17) | ![HB Köge HB Köge](https://tmssl.akamaized.net/images/wappen/verysmall/23297.png?lm=1429211362) | - |
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| 21.06.1999 (18) | ![NAC Breda NAC Breda](https://tmssl.akamaized.net/images/wappen/verysmall/132.png?lm=1667313213) | - |
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| 01.07.1999 (17) | ![Wieczysta Krakau Wieczysta Krakau](https://tmssl.akamaized.net/images/wappen/verysmall/30974.png?lm=1688323400) | 100 Tsd. € |
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| 29.01.1999 (18) | ![Heracles Almelo Heracles Almelo](https://tmssl.akamaized.net/images/wappen/verysmall/1304.png?lm=1488213735) | - |
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| 30.09.1999 (17) | ![PSV Eindhoven PSV Eindhoven](https://tmssl.akamaized.net/images/wappen/verysmall/383.png?lm=1682925949) | - |
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| 07.01.1999 (18) | ![Fortuna Sittard Fortuna Sittard](https://tmssl.akamaized.net/images/wappen/verysmall/385.png?lm=1610789891) | - |
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| 02.07.1999 (17) | ![Brescia Calcio Brescia Calcio](https://tmssl.akamaized.net/images/wappen/verysmall/19.png?lm=1511961167) | - |
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| 21.12.1999 (17) | ![Fortuna Sittard Fortuna Sittard](https://tmssl.akamaized.net/images/wappen/verysmall/385.png?lm=1610789891) | 150 Tsd. € |
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| 25.12.1999 (17) | ![FK Zalgiris Vilnius FK Zalgiris Vilnius](https://tmssl.akamaized.net/images/wappen/verysmall/602.png?lm=1475601977) | 100 Tsd. € |
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| 04.07.1999 (17) | ![Fortuna Sittard Fortuna Sittard](https://tmssl.akamaized.net/images/wappen/verysmall/385.png?lm=1610789891) | - |
- |
| 03.01.1999 (18) | ![União Leiria União Leiria](https://tmssl.akamaized.net/images/wappen/verysmall/2639.png?lm=1673648041) | - |
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| 05.05.1999 (18) | ![AFC Bournemouth AFC Bournemouth](https://tmssl.akamaized.net/images/wappen/verysmall/989.png?lm=1457991811) | 3,00 Mio. € |
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| 17.06.1999 (18) | ![PSV Eindhoven PSV Eindhoven](https://tmssl.akamaized.net/images/wappen/verysmall/383.png?lm=1682925949) | 100 Tsd. € |
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| 07.05.1999 (18) | ![FC Liverpool FC Liverpool](https://tmssl.akamaized.net/images/wappen/verysmall/31.png?lm=1456567819) | 50 Tsd. € |
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| 04.02.1999 (18) | ![SC Heerenveen SC Heerenveen](https://tmssl.akamaized.net/images/wappen/verysmall/306.png?lm=1655978084) | 50 Tsd. € |
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| 19.01.1999 (18) | ![Borussia Dortmund Borussia Dortmund](https://tmssl.akamaized.net/images/wappen/verysmall/16.png?lm=1396275280) | - |
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| 25.01.1999 (18) | ![SV TEC Tiel SV TEC Tiel](https://tmssl.akamaized.net/images/wappen/verysmall/12652.png?lm=1593591496) | - |
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| 02.08.1999 (17) | ![Leeds United Leeds United](https://tmssl.akamaized.net/images/wappen/verysmall/399.png?lm=1645652224) | 200 Tsd. € |
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| 09.05.1999 (18) | ![Hibernian FC Hibernian FC](https://tmssl.akamaized.net/images/wappen/verysmall/903.png?lm=1534336641) | 100 Tsd. € |
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| 05.03.1999 (18) | ![Helmond Sport Helmond Sport](https://tmssl.akamaized.net/images/wappen/verysmall/500.png?lm=1619786318) | 25 Tsd. € |