USA: US Open - Doubles - Main |
| 1/16-finals | Barnard M./Middleton T. J. | Coetzee J./Haygarth B. | 1:2 (4:6, 6:3, 5:7) | details | 03.09.1999 |
| 1/32-finals | Barnard M./Middleton T. J. | Pala P./Vizner P. | 2:0 (6:3, 7:65) | details | 01.09.1999 |
USA: Boston - Doubles - Main |
| Final | Barnard M./Middleton T. J. | Canas G./Garcia M. | 1:2 (7:5, 62:7, 3:6) | details | 26.08.1999 |
| Semi-finals | Pavel A./VanHoudt T. | Barnard M./Middleton T. J. | 0:2 (3:6, 5:7) | details | 25.08.1999 |
| Quarter-finals | Barnard M./Middleton T. J. | Kilderry P./Raoux G. | 2:1 (63:7, 6:2, 7:67) | details | 24.08.1999 |
| 1/8-finals | Barnard M./Middleton T. J. | Sprengelmeyer M./Weir-Smith J. | 2:0 (6:4, 6:3) | details | 23.08.1999 |
USA: Washington - Doubles - Main |
| Quarter-finals | Barnard M./Middleton T. J. | Gimelstob J./Lareau S. | 0:2 (4:6, 4:6) | details | 19.08.1999 |
| 1/8-finals | Arthurs W./Kratzmann A. | Barnard M./Middleton T. J. | 0:2 (4:6, 3:6) | details | 18.08.1999 |
| 1/16-finals | Barnard M./Middleton T. J. | Godwin N./Ondruska M. | 2:0 (7:5, 6:4) | details | 16.08.1999 |
United Kingdom: Wimbledon - Mixed Doubles - Main |
| 1/32-finals | Middleton T. J./McNeil L. | Woodbridge T./Davenport L. | 0:2 (4:6, 2:6) | details | 29.06.1999 |
United Kingdom: Wimbledon - Doubles - Main |
| 1/32-finals | Grant G./Middleton T. J. | Ferreira E./Leach R. | 0:3 (5:7, 65:7, 61:7) | details | 28.06.1999 |
United Kingdom: Nottingham - Doubles - Main |
| 1/8-finals | Middleton T. J./Waite J. | Broad N./Bale L. | 0:2 (3:6, 4:6) | details | 14.06.1999 |
United Kingdom: London - Doubles - Main |
| 1/8-finals | Middleton T. J./Tebbutt M. | Lareau S./O'Brien A. | 0:2 (2:6, 6:7) | details | 08.06.1999 |
| 1/16-finals | Santoro F./Tieleman L. | Middleton T. J./Tebbutt M. | 1:2 (6:4, 4:6, 3:6) | details | 07.06.1999 |
France: French Open - Doubles - Main |
| 1/32-finals | Grant G./Middleton T. J. | Albano P./Carbonell T. | 0:2 (2:6, 1:6) | details | 25.05.1999 |
USA: Delray Beach - Doubles - Main |
| Semi-finals | Grant G./Middleton T. J. | Flach D./MacPhie B. | 0:2 (6:7, 4:6) | details | 06.05.1999 |
| Quarter-finals | Grant G./Middleton T. J. | Coupe B./Merklein M. | 2:0 (6:4, 7:5) | details | 04.05.1999 |
| 1/8-finals | Bryan B./Bryan M. | Grant G./Middleton T. J. | 0:2 (2:6, 3:6) | details | 03.05.1999 |
Japan: Tokyo - Doubles - Main |
| 1/8-finals | Grant G./Middleton T. J. | Tarango J./Vacek D. | 1:2 (6:2, 6:7, 2:6) | details | 14.04.1999 |
| 1/16-finals | Grant G./Middleton T. J. | Kohlmann M./Veglio F. | 2:0 (6:4, 6:4) | details | 12.04.1999 |
India: Chennai - Doubles - Main |
| Quarter-finals | Knippschild J./Tillstrom M. | Grant G./Middleton T. J. | 2:0 (6:4, 6:0) | details | 08.04.1999 |
| 1/8-finals | Grant G./Middleton T. J. | Syed F./Sargsian S. | 2:0 (6:3, 6:3) | details | 06.04.1999 |
USA: Miami - Doubles - Main |
| 1/16-finals | Grant G./Middleton T. J. | Woodforde M./Woodbridge T. | 0:2 (4:6, 4:6) | details | 17.03.1999 |
| 1/32-finals | Grant G./Middleton T. J. | Bowen D./Godwin N. | 2:0 (6:1, 6:4) | details | 15.03.1999 |
USA: Memphis - Doubles - Main |
| Quarter-finals | Lareau S./O'Brien A. | Grant G./Middleton T. J. | 2:0 (6:3, 6:4) | details | 18.02.1999 |
| 1/8-finals | Grant G./Middleton T. J. | Tarango J./Vacek D. | 2:0 (7:5, 7:5) | details | 16.02.1999 |
| 1/16-finals | Albano P./Orsanic D. | Grant G./Middleton T. J. | 0:2 (6:7, 4:6) | details | 15.02.1999 |
USA: San Jose - Doubles - Main |
| 1/8-finals | Coupe B./Roditi D. | Haygarth B./Middleton T. J. | 2:1 (7:5, 6:7, 7:5) | details | 08.02.1999 |
Australia: Australian Open - Doubles - Main |
| 1/16-finals | Ferreira E./Leach R. | Haygarth B./Middleton T. J. | 2:0 (6:3, 6:4) | details | 20.01.1999 |
| 1/32-finals | Haygarth B./Middleton T. J. | Del Rio D./Puerta M. | 2:1 (6:4, 65:7, 15:13) | details | 18.01.1999 |
New Zealand: Auckland - Doubles - Main |
| Semi-finals | Grant G./Middleton T. J. | Tarango J./Vacek D. | 1:2 (3:6, 6:3, 3:6) | details | 15.01.1999 |
| Quarter-finals | Greenhalgh J./Steven B. | Grant G./Middleton T. J. | 0:2 (5:7, 4:6) | details | 13.01.1999 |
| 1/8-finals | Barnard M./Rosner P. | Grant G./Middleton T. J. | 0:2 (4:6, 4:6) | details | 11.01.1999 |
Colombia: Bogota - Doubles - Main |
| Quarter-finals | Novak J./Rikl D. | Albano P./Middleton T. J. | 2:0 (6:3, 6:4) | details | 04.11.1998 |
| 1/8-finals | Ruah M./Sa A. | Albano P./Middleton T. J. | 1:2 (7:6, 3:6, 4:6) | details | 02.11.1998 |
Mexico: Mexico City - Doubles - Main |
| Quarter-finals | Orsanic D./Roditi D. | Haygarth B./Middleton T. J. | 2:1 (5:7, 6:1, 6:4) | details | 28.10.1998 |
| 1/8-finals | Haygarth B./Middleton T. J. | Bale L./Sapsford D. | 2:1 (6:1, 4:6, 6:3) | details | 26.10.1998 |
Singapore: Singapore - Doubles - Main |
| 1/8-finals | Keil M./Middleton T. J. | Bhupathi M./Paes L. | 0:2 (4:6, 3:6) | details | 13.10.1998 |
China: Shanghai 2 - Doubles - Main |
| Quarter-finals | Woodforde M./Woodbridge T. | Keil M./Middleton T. J. | 2:0 (6:2, 6:1) | details | 07.10.1998 |
| 1/8-finals | Braasch K./Kohlmann M. | Keil M./Middleton T. J. | 0:2 (6:7, 4:6) | details | 05.10.1998 |
USA: Boston - Doubles - Main |
| Quarter-finals | Albano P./Lapentti N. | Keil M./Middleton T. J. | 2:1 (4:6, 7:6, 6:3) | details | 26.08.1998 |
USA: New Haven 2 - Doubles - Main |
| 1/16-finals | Goellner M./Prinosil D. | Keil M./Middleton T. J. | 2:0 (6:3, 6:3) | details | 17.08.1998 |
United Kingdom: Wimbledon - Mixed Doubles - Main |
| 1/16-finals | Stolle S./Kunce K. | Middleton T. J./McNeil L. | 2:0 (7:5, 6:3) | details | 26.06.1998 |
United Kingdom: Wimbledon - Doubles - Main |
| 1/32-finals | Keil M./Middleton T. J. | Knowles M./Nestor D. | 0:2 (67:7, 2:6) | details | 24.06.1998 |
United Kingdom: Wimbledon - Mixed Doubles - Main |
| 1/32-finals | Middleton T. J./McNeil L. | Kinnear K./Smith N. | 2:0 (7:67, 7:64) | details | 24.06.1998 |
United Kingdom: Nottingham - Doubles - Main |
| Semi-finals | Keil M./Middleton T. J. | Lareau S./Nestor D. | 0:2 (3:6, 3:6) | details | 20.06.1998 |
| Quarter-finals | De Jager J./Goellner M. | Keil M./Middleton T. J. | 1:2 (6:3, 6:7, 6:7) | details | 17.06.1998 |
| 1/8-finals | Keil M./Middleton T. J. | Cowan B./Petchey M. | 2:0 (6:1, 6:4) | details | 15.06.1998 |