| * All doubles with Tim Henman. |
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| Week Begin: | Tournament: | Round: | Opponent: | Score: |
| 25.10.99 | Stuttgart | Three | Tommy Haas | 6-3 6-4 |
| Qtr-Final | Todd Martin | 4-6 7-6 6-4 | ||
| Semi-Final | Richard Krajicek | 4-6 4-6 | ||
| 11.10.99 | Vienna | One | Thomas Johansson | 4-6 6-3 7-6 |
| Two | Andrei Medvedev | 4-6 7-5 6-3 | ||
| Qtr-Final | Sebastian Grosjean | 7-5 6-2 | ||
| Semi-Final | Roger Federer | 6-3 6-4 | ||
| Final | Nicholas Kiefer | 6-7 2-6 6-3 7-5 6-4 | ||
| 4.10.99 | Basel | One | Fabrice Santoro | 7-6 6-2 |
| Two | Dominic Hrbaty | 6-2 6-2 | ||
| Qtr-Final | Nicholas Kiefer | 6-2 6-7 3-6 | ||
| 27.9.99 | Grand Slam Cup | One | Gustavo Kuerten | 6-3 3-6 6-3 |
| Qtr-Final | Yevgeny Kafelnikov | 7-5 7-6 | ||
| Semi-Final | Andrei Medvedev | 6-3 3-6 7-6 7-5 | ||
| Final | Tommy Haas | 6-3 6-4 6-7 7-6 | ||
| 13.9.99 | Tashkent | One | Laurence Tieleman | 3-6- 4-6 |
| 30.8.99 | US Open | One | Juan Carlos Ferrero | 4-6 6-2 6-3 6-4 |
| Two | David Prinosil | 6-4 6-3 6-1 | ||
| Three | Chris Woodruff | 7-5 3-6 6-3 6-4 | ||
| Four | Todd Martin | 7-5 6-0 6-7(3) 4-6 4-6 | ||
| 23.8.99 | Boston | One | Kenneth Carlsen | 6-7(3) 6-2 7-5 |
| Two | Salon Pappas | 6-3 6-3 | ||
| Qtr-Final | Jonas Bjorkman | 7-5 6-3 | ||
| Semi-Final | Arnaud Clement | 6-4 5-7 6-2 | ||
| Final | Marat Safin | 4-6 6-7(11) | ||
| 5.7.99 | Gstaad | One | Marc Rosset | 6-7(2) 7-6(4) 2-6 |
| 21.6.99 | Wimbledon | One | Jason Stoltenberg | 6-4 6-1 6-2 |
| Two | Arvind Parmar | 6-3 6-4 7-6(3) | ||
| Three | Magnus Norman | 6-3 6-4 7-5 | ||
| Four | Mark Phillipoussis | 6-2 6-7(4) 3-6 1-6 | ||
| 14.6.99 | Nottingham | One | Gianluca Pozzi | 6-0 6-0 |
| Two | Jan Michael Gambill | 4-6 6-4 7-5 | ||
| Quarter Final | Lleyton Hewitt | 6-4 7-5 | ||
| Semi Final | Cedric Pioline | 4-6 6-7(4) | ||
| 7.6.99 | Queens Club, London | Two | Paul Goldstein | 6-3 6-4 |
| Three | Wayne Ferreira | 7-5 4-6 6-3 | ||
| Quarter Final | Sargis Sargsian | 2-6 4-6 | ||
| 24.5.99 | French Open | One | David Prinosil | 6-4 6-4 6-7 6-4 |
| Two | Richard Fromberg | 6-4 4-6 6-2 6-3 | ||
| Three | Davide Sanguinetti | 6-2 7-6(7) 6-2 | ||
| Four | Marcelo Filippini | 6-7(8) 3-6 4-6 | ||
| 16.5.99 | World Team Cup | Germany Singles | Nicholas Kiefer | 6-1 6-4 |
| Germany Doubles | Prinosil & Becker | 7-5 6-2 | ||
| Spain Singles | Alex Corretja | 5-7 6-3 3-6 | ||
| Spain Doubles | Costa & Velasco | 6-0 6-3 | ||
| Sweden Singles | Jonas Bjorkman | 2-6 2-6 | ||
| Sweden Doubles | Bjorkman & Kulti | 6-3 5-7 1-6 | ||
| 10.5.99 | Rome | One | Scott Draper | 7-6(4) 7-6(3) |
| Two | Nicholas Lapentti | 3-6 3-6 | ||
| 3.5.99 | Hamburg | Two | Alberto Berasetegui | 6-4 7-5 |
| Doubles | One | Meligeni/Montana | 2-6 6-4 5-7 | |
| 19.4.99 | Monte Carlo | Two | Jiri Novak | 2-6 2-6 |
| 15.3.99 | The Liptons, Key Biscayne | Two | Adrian Voinea | 6-4 6-4 |
| Three | Henrick Dreekman | 6-3 6-4 | ||
| Qtr-Final | Nicholas Kiefer | 6-4 5-7 2-6 | ||
| 8.3.99 | Indian Wells | One | Petr Korda | 6-3 6-4 |
| Two | Scott Draper | 6-3 6-3 | ||
| Three | Tim Henman | 4-6 6-2 4-6 | ||
| 22.2.99 | Battersea, London | One | Gianluca Pozzi | 6-2 6-1 |
| Two | Petr Korda | 6-3 7-6(4) | ||
| Qtr Final | Thomas Enqvist | 7-5 4-6 6-3 | ||
| Semi Final | Hicham Arazi | 6-2 6-3 | ||
| Final | Krajicek | 6-7(6) 7-6(5) 5-7 | ||
| Doubles | One | Ullyatt/Norval | 7-5(5) 6-2 | |
| Qtr-Final | Broad/Koenig | 6-4 6-4 | ||
| Semi-Final | Kafelnikov/Vacek | 6-4 6-4 | ||
| Final | Ferreira/Black(B) | 6-3 7-6(6) | ||
| 15.2.99 | Rotterdam | One | Nicholas Kiefer | 7-6(5) 4-6 6-3 |
| Two | Ed Kempers | 6-1 6-4 | ||
| Qtr-Final | Cedric Pioline | 7-6(5) 3-6 7-6(5) | ||
| Semi-Final | Yevgeny Kafelnikov | 4-6 2-6 | ||
| 8.2.99 | Dubai Open | One | Sjeng Schalken | 6-3 6-4 |
| Two | Francisco Clavet | 6-3 5-7 2-6 | ||
| 18.1.99 | Australian Open | One | Scott Draper | 7-6(3) 2-6 6-4 7-6(5) |
| Two | Paul Goldstein | 4-6 7-6(9) 6-7(5) 2-6 | ||
| 11.1.99 | Sydney | One | Gustavo Keurten | 6-1 3-6 4-6 |
| 4.1.99 | Qatar Open, Doha | One | Bernd Karbacher | 6-4 6-7 3-6 |