| Singles | |
|---|---|
| 1999 Guardian Direct Cup | |
| Champions |  Richard Krajicek [1] |
| Runners-up |  Greg Rusedski |
| Score | 7–6(8–6), 6–7(5–7), 7–5 |
| Draw | 32 |
| Seeds | 8 |
The 1999 Guardian Direct Cup was a men's tennis tournament played on indoor carpet courts in London, Great Britain, that was part of the Championship Series of the 1999 ATP Tour. It was the 22nd edition of the tournament and was held from 22 February until 28 February 1999.
Champion seeds are indicated in bold text while text in italics indicates the round in which those seeds were eliminated.
Yevgeny Kafelnikov (quarterfinals) Tim Henman (first round) Greg Rusedski (final) Richard Krajicek (champion)
Karol Kučera (quarterfinals)
Thomas Enqvist (quarterfinals)
Goran Ivanišević (second round) Thomas Johansson (semifinals)| Semifinals | Final [1] | ||||||||||||
| 8 | Thomas Johansson | 2 | 4 | ||||||||||
| 4 | Richard Krajicek | 6 | 6 | ||||||||||
| 4 | Richard Krajicek | 7 | 65 | 7 | |||||||||
| 3 | Greg Rusedski | 66 | 7 | 5 | |||||||||
| 3 | Greg Rusedski | 6 | 6 | ||||||||||
 Hicham Arazi | 2 | 3 | |||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 1 | Y Kafelnikov | 6 | 3 | 6 | |||||||||||||||||||||||
| M Gustafsson | 2 | 6 | 3 | 1 | Y Kafelnikov | 6 | 6 | ||||||||||||||||||||
 B Black | 6 | 1 | 7 | B Black | 3 | 2 | |||||||||||||||||||||
| K Alami | 1 | 6 | 64 | 1 | Y Kafelnikov | 2 | 65 | ||||||||||||||||||||
 D Sanguinetti | 6 | 6 | 8 | T Johansson | 6 | 7 | |||||||||||||||||||||
 J-M Gambill | 4 | 4 | D Sanguinetti | 0 | 7 | 2 | |||||||||||||||||||||
| 8 | T Johansson | 6 | 6 | 8 | T Johansson | 6 | 63 | 6 | |||||||||||||||||||
 P Luxa | 2 | 4 | 8 | T Johansson | 2 | 4 | |||||||||||||||||||||
| 4 | R Krajicek | 6 | 6 | 4 | R Krajicek | 6 | 6 | ||||||||||||||||||||
| J Tarango | 4 | 2 | 4 | R Krajicek | 6 | 6 | |||||||||||||||||||||
 N Kiefer | 5 | 6 | 7 | N Kiefer | 3 | 4 | |||||||||||||||||||||
 C Pioline | 7 | 2 | 5 | 4 | R Krajicek | 6 | 6 | ||||||||||||||||||||
| G Raoux | 6 | 6 | 5 | K Kučera | 1 | 3 | |||||||||||||||||||||
| D Vacek | 4 | 3 | G Raoux | 2 | 0 | ||||||||||||||||||||||
| 5 | K Kučera | 7 | 6 | 5 | K Kučera | 6 | 6 | ||||||||||||||||||||
| R Schüttler | 62 | 0 | |||||||||||||||||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 6 | T Enqvist | 6 | 6 | ||||||||||||||||||||||||
 M Rosset | 1 | 3 | 6 | T Enqvist | 6 | 7 | |||||||||||||||||||||
| D Prinosil | 7 | 6 | D Prinosil | 4 | 5 | ||||||||||||||||||||||
 A Pavel | 65 | 3 | 6 | T Enqvist | 5 | 6 | 3 | ||||||||||||||||||||
| P Korda | 6 | 6 | 3 | G Rusedski | 7 | 4 | 6 | ||||||||||||||||||||
 W Ferreira | 3 | 4 | P Korda | 3 | 64 | ||||||||||||||||||||||
| 3 | G Rusedski | 6 | 6 | 3 | G Rusedski | 6 | 7 | ||||||||||||||||||||
| G Pozzi | 2 | 1 | 3 | G Rusedski | 6 | 6 | |||||||||||||||||||||
| 7 | G Ivanišević | 6 | 0 | 7 | H Arazi | 2 | 3 | ||||||||||||||||||||
| J Siemerink | 3 | 6 | 61 | 7 | G Ivanišević | 6 | 3 | 4 | |||||||||||||||||||
| H Arazi | 7 | 6 | H Arazi | 3 | 6 | 6 | |||||||||||||||||||||
| B Ulihrach | 5 | 4 | H Arazi | 6 | 6 | ||||||||||||||||||||||
| D Hrbatý | 6 | 63 | 6 | D Hrbatý | 4 | 2 | |||||||||||||||||||||
| S Pescosolido | 3 | 7 | 2 | D Hrbatý | 6 | 6 | |||||||||||||||||||||
| J Krošlák | 2 | 7 | 6 | J Krošlák | 2 | 3 | |||||||||||||||||||||
| 2 | T Henman | 6 | 68 | 4 | |||||||||||||||||||||||
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