1999–2000 AFC Ajax season

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During the 1999–2000 Dutch football season, Ajax competed in the Eredivisie.

Another poor season saw Ajax finish in fifth, though this at least was an improvement on finishing sixth the previous season.

Squad at end of season. Squad numbers refer to numbers worn in European competitions.

Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply. Players may hold more than one non-FIFA nationality.

No. Pos. Nation Player 1 GK  NED Fred Grim 2 DF  DEN Ole Tobiasen 3 DF  NED Ferdi Vierklau 4 DF  NED Jan van Halst 5 DF  NED Frank Verlaat 6 MF  NED Aron Winter (captain) 7 FW  BRA Wamberto 8 MF  NED Richard Witschge 9 FW  GRE Nikos Machlas 10 FW  DEN Brian Laudrup 11 MF  DEN Jesper Grønkjær 13 MF  NED Richard Knopper 14 FW  POR Dani 15 DF  NED Tim de Cler 16 DF  NED John Nieuwenburg 17 DF  ROU Cristian Chivu

No. Pos. Nation Player 18 MF  USA John O'Brien 19 FW  NGA Tijani Babangida 21 MF  NGA Pius Ikedia 23 MF  NED Martijn Reuser 24 FW  GEO Shota Arveladze 25 DF  NGA Christopher Kanu 26 FW  NED Brutil Hosé[notes 1] 28 GK  NED Serge van den Ban 29 FW  NED Kevin Bobson 30 DF  NED Mitchell Piqué 36 DF  NED Quido Lanzaat 37 MF  RSA Aaron Mokoena 42 MF  GHA Abubakari Yakubu 43 MF  NED Rafael van der Vaart

Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply. Players may hold more than one non-FIFA nationality.

No. Pos. Nation Player 27 MF  NED Cedric van der Gun (on loan to Den Bosch) — MF  NED Peter Hoekstra (on loan to Compostela)

No. Pos. Nation Player — MF  NED Andy van der Meyde (on loan to Twente)

Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply. Players may hold more than one non-FIFA nationality.

No. Pos. Nation Player — GK  NED Maarten Stekelenburg — DF  NED Serginho Greene — DF  NED John Heitinga — MF  NED Nigel de Jong

No. Pos. Nation Player — MF  NED Jeffrey Sneijder — MF  NED Wesley Sneijder — MF  COL Daniel Cruz

• Danny Blind - retired
• Gerald Sibon - Sheffield Wednesday, £2,000,000
• Kofi Mensah^{[notes 2]} - NAC Breda
• Dean Gorré - Huddersfield Town
• Mario Melchiot - Chelsea, free^[1]
• Andrzej Rudy - Lierse
• Sunday Oliseh - Juventus
• Jari Litmanen - Barcelona

Hapoel Haifa v Ajax

21 October 1999	Hapoel Haifa	0–3	Ajax	Kiryat Eliezer Stadium, Haifa
		Report	Machlas 3' Knopper 12' Laudrup 55'	Attendance: 14,500 Referee: Tomasz Mikulski (Poland)

Ajax v Hapoel Haifa

4 November 1999	Ajax	0–1	Hapoel Haifa	Amsterdam Arena, Amsterdam
		Report	Roso 60'	Attendance: 37,400 Referee: Knud Erik Fisker (Denmark)

Ajax won 3–1 on aggregate.

Ajax v Mallorca

25 November 1999	Ajax	0–1	Mallorca	Amsterdam Arena, Amsterdam
		Report	Tristán 35'	Attendance: 40,123 Referee: Ľuboš Micheľ (Slovakia)

Mallorca v Ajax

9 December 1999	Mallorca	2–0	Ajax	Son Moix, Palma
	Soler 2' Biagini 70'	Report		Attendance: 20,500 Referee: Fritz Stuchlik (Austria)

Mallorca won 3–0 on aggregate.