| MD | Players | Clubs | Nationality | DOB | A(D) |
|---|---|---|---|---|---|
| 03-Jan-1999 |  Michael Owen | Liverpool | England | 14-Dec-1979 | 19(20) |
| 11-Apr-1999 |  Nicolas Anelka | Arsenal | France | 14-Mar-1979 | 20(28) |
| 22-May-1999 |  Andy Griffin | Newcastle United | England | 17-Mar-1979 | 20(66) |
| 03-Jan-1999 | Jamie Carragher | Liverpool | England | 28-Jan-1978 | 20(340) |
| 03-Jan-1999 |  Neil Brisco | Port Vale | England | 26-Jan-1978 | 20(342) |
| 22-May-1999 | Didier Domi | Newcastle United | France | 02-May-1978 | 21(20) |
| 03-Jan-1999 | Michael Walsh | Port Vale | England | 05-Aug-1977 | 21(151) |
| 11-Apr-1999 | Fredrik Ljungberg | Arsenal | Sweden | 16-Apr-1977 | 21(360) |
| 14-Apr-1999 |  Phil Neville | Manchester United | England | 21-Jan-1977 | 22(83) |
| 11-Apr-1999 | Nwankwo Kanu | Arsenal | Nigeria | 01-Aug-1976 | 22(253) |
| 11-Apr-1999 | Patrick Vieira | Arsenal | France | 23-Jun-1976 | 22(292) |
| 22-May-1999 | Stephen Glass | Newcastle United | Scotland | 23-May-1976 | 22(364) |
| 24-Jan-1999 | Vegard Heggem | Liverpool | Norway | 13-Jul-1975 | 23(195) |
| 24-Jan-1999 | David Beckham | Manchester United | England | 02-May-1975 | 23(267) |
| 24-Jan-1999 | Robbie Fowler | Liverpool | England | 09-Apr-1975 | 23(290) |
| 24-Jan-1999 | Gary Neville | Manchester United | England | 18-Feb-1975 | 23(340) |
| 24-Jan-1999 | Nicky Butt | Manchester United | England | 21-Jan-1975 | 24(3) |
| 22-May-1999 | Silvio Maric | Newcastle United | Croatia | 20-Mar-1975 | 24(63) |
| 22-May-1999 | Steve Harper | Newcastle United | England | 14-Mar-1975 | 24(69) |
| 11-Apr-1999 | Paul Scholes | Manchester United | England | 16-Nov-1974 | 24(146) |
| 22-May-1999 | Nolberto Solano | Newcastle United | Peru | 12-Dec-1974 | 24(161) |
| 24-Jan-1999 | Dominic Matteo | Liverpool | Scotland | 24-Apr-1974 | 24(275) |
| 03-Jan-1999 | Kevin Pilkington | Port Vale | England | 08-Mar-1974 | 24(301) |
| 03-Jan-1999 | Patrik Berger | Liverpool | Czech Republic | 10-Nov-1973 | 25(54) |
| 24-Jan-1999 | Ryan Giggs | Manchester United | Wales | 29-Nov-1973 | 25(56) |
| 14-Apr-1999 | Jesper Blomqvist | Manchester United | Sweden | 05-Feb-1974 | 25(68) |
| 03-Jan-1999 | Jamie Redknapp | Liverpool | England | 25-Jun-1973 | 25(192) |
| 22-May-1999 | Dietmar Hamann | Newcastle United | Germany | 27-Aug-1973 | 25(268) |
| 22-May-1999 | Nikos Dabizas | Newcastle United | Greece | 03-Aug-1973 | 25(292) |
| 24-Jan-1999 | Ole-Gunnar Solskjaer | Manchester United | Norway | 26-Feb-1973 | 25(332) |
| 11-Apr-1999 | Marc Overmars | Arsenal | Netherlands | 29-Mar-1973 | 26(13) |
| 22-May-1999 | Laurent Charvet | Newcastle United | France | 08-May-1973 | 26(14) |
| 11-Apr-1999 | Ray Parlour | Arsenal | England | 07-Mar-1973 | 26(35) |
| 24-Jan-1999 | Jaap Stam | Manchester United | Netherlands | 17-Jul-1972 | 26(191) |
| 24-Jan-1999 | Dwight Yorke | Manchester United | Trinidad and Tobago | 03-Nov-1971 | 27(82) |
| 24-Jan-1999 | Andrew Cole | Manchester United | England | 15-Oct-1971 | 27(101) |
| 03-Jan-1999 | Steve Harkness | Liverpool | England | 27-Aug-1971 | 27(129) |
| 22-May-1999 | Duncan Ferguson | Newcastle United | Scotland | 27-Dec-1971 | 27(146) |
| 24-Jan-1999 | Roy Keane | Manchester United | Republic of Ireland | 10-Aug-1971 | 27(167) |
| 03-Jan-1999 | Jason McAteer | Liverpool | Republic of Ireland | 18-Jun-1971 | 27(199) |
| 03-Jan-1999 | Phil Babb | Liverpool | Republic of Ireland | 30-Nov-1970 | 28(34) |
| 03-Jan-1999 | David James | Liverpool | England | 01-Aug-1970 | 28(155) |
| 14-Apr-1999 | Emmanuel Petit | Arsenal | France | 22-Sep-1970 | 28(204) |
| 22-May-1999 | Alan Shearer | Newcastle United | England | 13-Aug-1970 | 28(282) |
| 22-May-1999 | David May | Manchester United | England | 24-Jun-1970 | 28(332) |
| 03-Jan-1999 | Stig Inge Bjornebye | Liverpool | Norway | 11-Dec-1969 | 29(23) |
| 24-Jan-1999 | Henning Berg | Manchester United | Norway | 01-Sep-1969 | 29(145) |
| 11-Apr-1999 | Nelson Vivas | Arsenal | Argentina | 18-Oct-1969 | 29(175) |
| 24-Jan-1999 | Ronny Johnsen | Manchester United | Norway | 10-Jun-1969 | 29(228) |
| 22-May-1999 | Gary Speed | Newcastle United | Wales | 08-Sep-1969 | 29(256) |
MD = Match date,
DOB = Date Of Birth,
A(D) = Age(Days).