202720262025202420232022202120202019201820172016201520142013201220112010200920082007200620052004200320022001200019991998199719961995All competitions Premier League League CupGameplan DateRoundMatchMatchRes.Attendance09.01.1999Matchday 21Middlesbrough - Aston VillaMID - AVL0:034.64330.01.1999Matchday 23Middlesbrough - LeicesterMID - LEI0:034.63120.02.1999Matchday 26Middlesbrough - TottenhamMID - TOT0:034.68714.03.1999Matchday 29Middlesbrough - SouthamptonMID - SOU3:033.38705.04.1999Matchday 32Middlesbrough - Wimbledon FCMID - 3:133.99910.04.1999Matchday 33Middlesbrough - Charlton Athl.MID - CHA2:034.52914.04.1999Matchday 28Middlesbrough - ChelseaMID - CHE0:034.40624.04.1999Matchday 35Middlesbrough - ArsenalMID - ARS1:634.63009.05.1999Matchday 37Middlesbrough - Man UtdMID - MUN0:134.66507.08.1999Matchday 1Middlesbrough - BradfordMID - BRA0:133.76221.08.1999Matchday 4Middlesbrough - LiverpoolMID - LIV1:034.78324.08.1999Matchday 5Middlesbrough - LeicesterMID - LEI0:333.12611.09.1999Matchday 7Middlesbrough - SouthamptonMID - SOU3:232.16521.09.19992. Round 2nd legMiddlesbrough - Chesterfield FCMID - CHF2:125.60225.09.1999Matchday 9Middlesbrough - ChelseaMID - CHE0:134.18313.10.19993. RoundMiddlesbrough - WatfordMID - WAT1:08.84317.10.1999Matchday 11Middlesbrough - West HamMID - WHU2:031.86230.10.1999Matchday 13Middlesbrough - EvertonMID - EVE2:133.91606.11.1999Matchday 14Middlesbrough - SunderlandMID - SUN1:134.79327.11.1999Matchday 16Middlesbrough - Wimbledon FCMID - 0:031.40030.11.1999Round of 16Middlesbrough - ArsenalMID - ARS3:123.15718.12.1999Matchday 18Middlesbrough - TottenhamMID - TOT2:133.129