# 1999 Legg Mason Tennis Classic – Singles

Andre Agassi was the defending champion and won for the second straight year in the final 7–6$^{(7–3)}$, 6–1, over Yevgeny Kafelnikov.

## Seeds

* Yevgeny Kafelnikov (final)
* Andre Agassi (champion)
* Tim Henman (third round)
* Todd Martin (semifinals)
* Àlex Corretja (third round)
* Nicolas Kiefer (semifinals)
* Marc Rosset (third round)
* Marat Safin (third round)
* Fabrice Santoro (quarterfinals)
* Rainer Schüttler (second round)
* Jan-Michael Gambill (third round)
* Byron Black (first round)
* Michael Chang (second round)
* Ján Krošlák (quarterfinals)
* Richard Fromberg (first round)
* Marcelo Filippini (first round)

## Draw
### Key

* WC - Wildcard
* Q - Qualifier
* SE - Special Exempt
* r - Retired

### Finals

| Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals | Semifinals | Finals | Finals | Finals | Finals |
| 1 | Yevgeny Kafelnikov | 6 | 6$^7$ | 7 | | | | | | | | | |
| | Tomáš Zíb | 1 | 7$^9$ | 5 | | | | | | | | | |
| | Tomáš Zíb | 1 | 7$^9$ | 5 | 1 | Yevgeny Kafelnikov | 6 | 2 | 6 | | | | |
| | | | | | 6 | Nicolas Kiefer | 2 | 6 | 3 | | | | |
| 14 | Ján Krošlák | 4 | 3 | | 6 | Nicolas Kiefer | 2 | 6 | 3 | | | | |
| 6 | Nicolas Kiefer | 6 | 6 | | | | | | | | | | |
| 6 | Nicolas Kiefer | 6 | 6 | | | | | | | 1 | Yevgeny Kafelnikov | 6$^3$ | 1 |
| | | | | | | | | | | 2 | Andre Agassi | 7$^7$ | 6 |
| | Paul Goldstein | 4 | 5 | | | | | | | | | | | 2 | Andre Agassi | 7$^7$ | 6 |
| 4 | Todd Martin | 6 | 7 | | | | | | | | | | |
| 4 | Todd Martin | 6 | 7 | | 4 | Todd Martin | 4 | 2 | | | | | |
| | | | | | 2 | Andre Agassi | 6 | 6 | | | | | |
| 9 | Fabrice Santoro | 4 | 5 | | 2 | Andre Agassi | 6 | 6 | | | | | |
| 1 | Andre Agassi | 6 | 7 | | | | | | | | | | |

### Earlier rounds
#### Section 1

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| | | | | | 1 | Y Kafelnikov | 0 | 6 | 6 | | | | | | | | | |
| | O Gross | 3 | 1 | | | W Black | 6 | 2 | 4 | | | | | | | | | |
| | W Black | 6 | 6 | | | | | | | 1 | Y Kafelnikov | 7 | 6 | | | | | |
| WC | P Osuna | 4 | 1 | | | | | | | | J Gimelstob | 5 | 4 | | | | | |
| | W Arthurs | 6 | 6 | | | W Arthurs | 4 | 1 | | | | | | | | | | |
| | J Gimelstob | 6 | 2 | 7$^7$ | | J Gimelstob | 6 | 6 | | | | | | | | | | |
| 15 | R Fromberg | 4 | 6 | 6$^4$ | | | | | | | | | | 1 | Y Kafelnikov | 6 | 6$^7$ | 7 |
| 10 | R Schüttler | 6 | 7 | | | | | | | | | | | | T Zíb | 1 | 7$^9$ | 5 |
| | N Kulti | 1 | 5 | | 10 | R Schüttler | 7$^7$ | 5 | 0 | | | | | | | | | |
| | T Zíb | 7$^7$ | 7$^7$ | | | T Zíb | 6$^2$ | 7 | 3 | | | | | | | | | |
| | J Díaz | 6$^1$ | 6$^4$ | | | | | | | | T Zíb | 6 | 6 | | | | | |
| WC | I Ljubičić | 6 | 3 | 4 | | | | | | 7 | M Rosset | 3 | 2 | | | | | |
| WC | F González | 1 | 6 | 6 | WC | F González | 6$^9$ | 4 | | | | | | | | | | |
| | | | | | 7 | M Rosset | 7$^{11}$ | 6 | | | | | | | | | | |

#### Section 2

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| | | | | | 3 | T Henman | 7$^7$ | 7 | | | | | | | | | | |
| | P Wessels | 6 | 6 | | | P Wessels | 6$^2$ | 5 | | | | | | | | | | |
| WC | J Blake | 4 | 1 | | | | | | | 3 | T Henman | 6 | 3 | 4 | | | | |
| | L Manta | 2 | 6 | 6 | | | | | | 14 | J Krošlák | 3 | 6 | 6 | | | | |
| | T Suzuki | 6 | 4 | 2 | | L Manta | 5 | 6$^3$ | | | | | | | | | | |
| Q | B Ellwood | 2 | 4 | | 14 | J Krošlák | 7 | 7$^7$ | | | | | | | | | | |
| 14 | J Krošlák | 6 | 6 | | | | | | | | | | | | 14 | J Krošlák | 4 | 3 |
| 11 | J Gambill | 6$^3$ | 6 | 4 | | | | | | | | | | | 6 | N Kiefer | 6 | 6 |
| | K Carlsen | 7$^7$ | 4 | 6 | | K Carlsen | 4 | 6 | 6$^5$ | | | | | | | | | |
| | V Santopadre | 1 | 1 | | | J Lottum | 6 | 1 | 7$^7$ | | | | | | | | | |
| | J Lottum | 6 | 6 | | | | | | | | J Lottum | 5 | 2 | | | | | |
| Q | M Washington | 2 | 6 | 6 | | | | | | 6 | N Kiefer | 7 | 6 | | | | | |
| | J Chela | 6 | 3 | 4 | Q | M Washington | 4 | 2 | | | | | | | | | | |
| | | | | | 6 | N Kiefer | 6 | 6 | | | | | | | | | | |

#### Section 3

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| | | | | | 5 | À Corretja | 7$^7$ | 1 | 7 | | | | | | | | |
| | S Draper | 3 | 3 | | | G Pozzi | 6$^5$ | 6 | 5 | | | | | | | | |
| | G Pozzi | 6 | 6 | | | | | | | 5 | À Corretja | 6$^9$ | 6$^5$ | | | | |
| | P Goldstein | 7 | 6 | | | | | | | | P Goldstein | 7$^{11}$ | 7$^7$ | | | | |
| | C Mamiit | 5 | 4 | | | P Goldstein | 5 | 7 | 6 | | | | | | | | |
| | M Damm | 6 | 6 | | | M Damm | 7 | 5 | 2 | | | | | | | | |
| 12 | B Black | 2 | 2 | | | | | | | | | | | | Paul Goldstein | 4 | 5 |
| 13 | M Chang | 6 | 6 | | | | | | | | | | | 4 | Todd Martin | 6 | 7 |
| Q | N Zimonjić | 0 | 1 | | 13 | M Chang | 4 | 6 | 3 | | | | | | | | |
| Q | I Labadze | 6 | 6$^3$ | 1 | | R Delgado | 6 | 1 | 6 | | | | | | | | |
| | R Delgado | 3 | 7$^7$ | 6 | | | | | | | R Delgado | | | | | | |
| | A Voinea | 5 | 0 | | | | | | | 4 | Todd Martin | w/o | | | | | |
| WC | K Pless | 7 | 6 | | WC | K Pless | 4 | 4 | | | | | | | | | |
| | | | | | 4 | Todd Martin | 6 | 6 | | | | | | | | | |

#### Section 4

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| | | | | | 8 | M Safin | 7 | 7$^7$ | | | | | | | | | |
| | B Karbacher | 4 | 6 | 1 | | S Lareau | 5 | 6$^2$ | | | | | | | | | |
| | S Lareau | 6 | 3 | 6 | | | | | | 8 | M Safin | 0 | 4 | | | | |
| Q | K Ullyett | 7$^7$ | 6$^5$ | 3 | | | | | | 9 | Fabrice Santoro | 6 | 6 | | | | |
| | R Agénor | 6$^3$ | 7$^7$ | 6 | | R Agénor | 4 | 4 | | | | | | | | | |
| | H Gumy | 3 | 6 | 1 | 9 | Fabrice Santoro | 6 | 6 | | | | | | | | | |
| 9 | Fabrice Santoro | 6 | 3 | 6 | | | | | | | | | | 9 | Fabrice Santoro | 4 | 5 |
| 16 | M Filippini | 3 | 3 | | | | | | | | | | | 2 | Andre Agassi | 6 | 7 |
| | L Tieleman | 6 | 6 | | | L Tieleman | 6 | 3 | 4 | | | | | | | | |
| | R Federer | 2 | 3 | | Q | B Phau | 3 | 6 | 6 | | | | | | | | |
| Q | B Phau | 6 | 6 | | | | | | | Q | B Phau | 1 | 3 | | | | |
| WC | X Malisse | 3 | 6 | 5 | | | | | | 2 | Andre Agassi | 6 | 6 | | | | |
| Q | M Tillström | 6 | 3 | 7 | Q | M Tillström | 1 | 1 | | | | | | | | | |
| | | | | | 2 | Andre Agassi | 6 | 6 | | | | | | | | | |

## Qualifying
### Qualifying seeds

* Mikael Tillström (qualified)
* Kevin Ullyett (qualified)
* Marcos Ondruska (first round)
* Neville Godwin (qualifying competition)
* Michael Hill (qualifying competition)
* Nenad Zimonjić (qualified)
* Ivo Heuberger (first round)
* David Caldwell (first round)
* Michael Joyce (qualifying competition)
* Brian MacPhie (first round)
* Barry Cowan (first round)
* Michael Russell (first round)
* Mark Draper (qualifying competition)
* Frédéric Niemeyer (qualifying competition)

### Qualifiers

* Mikael Tillström
* Kevin Ullyett
* Irakli Labadze
* Björn Phau
* Mashiska Washington
* Nenad Zimonjić
* Ben Ellwood

### Qualifying draw
#### First qualifier

| First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 1 | Mikael Tillström | 6 | 6 | | | | | |
| WC | Thomas Blake | 2 | 2 | | | | | |
| WC | Thomas Blake | 2 | 2 | 1 | Mikael Tillström | 5 | 6 | 6 |
| | | | | 13 | Mark Draper | 7 | 3 | 1 |
| | Wesley Whitehouse | 4 | 3 | 13 | Mark Draper | 7 | 3 | 1 |
| 13 | Mark Draper | 6 | 6 | | | | | |

#### Second qualifier

| First round | First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 2 | Kevin Ullyett | 6 | 6 | | | | | |
| | Scott Humphries | 4 | 3 | | | | | |
| | Scott Humphries | 4 | 3 | | 2 | Kevin Ullyett | 6 | 6 |
| | | | | | 14 | Frédéric Niemeyer | 3 | 4 |
| | Simon Larose | 6 | 6 | 1 | 14 | Frédéric Niemeyer | 3 | 4 |
| 14 | Frédéric Niemeyer | 3 | 7 | 6 | | | | |

#### Third qualifier

| First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 3 | Marcos Ondruska | 4 | 2 | | | | |
| | Solon Peppas | 6 | 6 | | | | |
| | Solon Peppas | 6 | 6 | | Solon Peppas | 2 | 1 |
| | | | | WC | Irakli Labadze | 6 | 6 |
| WC | Irakli Labadze | 6 | 6 | WC | Irakli Labadze | 6 | 6 |
| 12 | Michael Russell | 1 | 4 | | | | |

#### Fourth qualifier

| First round | First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 4 | Neville Godwin | 6 | 6 | | | | | |
| WC | H'Cone Thompson | 1 | 0 | | | | | |
| WC | H'Cone Thompson | 1 | 0 | | 4 | Neville Godwin | 2 | 4 |
| | | | | | | Björn Phau | 6 | 6 |
| | Björn Phau | 6 | 3 | 7 | | Björn Phau | 6 | 6 |
| 10 | Brian MacPhie | 2 | 6 | 6 | | | | |

#### Fifth qualifier

| First round | First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 5 | Michael Hill | 6 | 4 | 7 | | | | |
| | Uros Vico | 4 | 6 | 6 | | | | |
| | Uros Vico | 4 | 6 | 6 | 5 | Michael Hill | 4 | 2 |
| | | | | | | Mashiska Washington | 6 | 6 |
| | Mashiska Washington | 5 | 6 | 6 | | Mashiska Washington | 6 | 6 |
| 11 | Barry Cowan | 7 | 3 | 3 | | | | |

#### Sixth qualifier

| First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 6 | Nenad Zimonjić | 6 | 6 | | | | | |
| | Steve Campbell | 3 | 4 | | | | | |
| | Steve Campbell | 3 | 4 | 6 | Nenad Zimonjić | 6 | 7 | 7 |
| | | | | | Bobby Kokavec | 7 | 6 | 6 |
| | Bobby Kokavec | 6 | 7 | | Bobby Kokavec | 7 | 6 | 6 |
| 8 | David Caldwell | 4 | 5 | | | | | |

#### Seventh qualifier

| First round | First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 7 | Ivo Heuberger | 3 | 6 | 6 | | | | |
| | Ben Ellwood | 6 | 3 | 7 | | | | |
| | Ben Ellwood | 6 | 3 | 7 | | Ben Ellwood | 6 | 6 |
| | | | | | 9 | Michael Joyce | 3 | 4 |
| WC | Torrey Gambill | 3 | 1 | | 9 | Michael Joyce | 3 | 4 |
| 9 | Michael Joyce | 6 | 6 | | | | | |