# 1999 Kremlin Cup – Men's singles

Yevgeny Kafelnikov was the defending champion and won in the final 7–6$^{(7–2)}$, 6–4 against Byron Black.

## Seeds

* Yevgeny Kafelnikov (champions)
* Vince Spadea (first round)
* Sébastien Grosjean (first round)
* Younes El Aynaoui (first round)
* Andriy Medvedev (quarterfinals)
* Marat Safin (first round)
* Marc Rosset (quarterfinals)
* Jiří Novák (first round)

## Draw
### Key

* Q = Qualifier
* WC = Wild card
* LL = Lucky loser
* Alt = Alternate
* SE = Special exempt
* PR = Protected ranking
* ITF = ITF entry
* JE = Junior exempt
* w/o = Walkover
* r = Retired
* d = Defaulted
* SR = Special ranking

### Finals

| Semifinals | Semifinals | Semifinals | Semifinals | Semifinals | Final | Final | Final | Final |
| 1 | Yevgeny Kafelnikov | 6$^4$ | 7$^7$ | 6 | | | | |
| | Nicolas Escudé | 7$^7$ | 6$^2$ | 4 | | | | |
| | Nicolas Escudé | 7$^7$ | 6$^2$ | 4 | 1 | Yevgeny Kafelnikov | 7$^7$ | 6 |
| | | | | | | Byron Black | 6$^2$ | 4 |
| | Byron Black | 6 | 6 | | | Byron Black | 6$^2$ | 4 |
| | Jeff Tarango | 3 | 2 | | | | | |

### Top half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals | Semifinals |
| 1 | Y Kafelnikov | 6 | 6 | | | | | | | | | | | | | | | | |
| | A Clément | 3 | 2 | | 1 | Y Kafelnikov | 6 | 7 | | | | | | | | | | | |
| | D Prinosil | 6 | 6 | | | D Prinosil | 4 | 5 | | | | | | | | | | | |
| | A Ilie | 3 | 2 | | | | | | | 1 | Y Kafelnikov | 7$^7$ | 6 | | | | | | |
| | D Vacek | 6 | 6 | | | | | | | | D Vacek | 6$^3$ | 3 | | | | | | |
| WC | M Youzhny | 1 | 4 | | | D Vacek | 6$^9$ | 6 | 7 | | | | | | | | | | |
| Q | C Saulnier | 2 | 7$^7$ | 6 | Q | C Saulnier | 7$^{11}$ | 3 | 5 | | | | | | | | | | |
| 8 | J Novák | 6 | 6$^3$ | 4 | | | | | | | | | | | 1 | Y Kafelnikov | 6$^4$ | 7$^7$ | 6 |
| 4 | Y El Aynaoui | 6$^3$ | 6$^5$ | | | | | | | | | | | | | N Escudé | 7$^7$ | 6$^2$ | 3 |
| | N Escudé | 7$^7$ | 7$^7$ | | | N Escudé | 6 | 3 | 6 | | | | | | | | | | |
| | J Krošlák | 5 | 7$^7$ | 7$^7$ | | J Krošlák | 1 | 6 | 3 | | | | | | | | | | |
| | J Siemerink | 7 | 6$^3$ | 6$^3$ | | | | | | | N Escudé | 2 | 6 | 6 | | | | | |
| | G Cañas | 3 | 7 | 6$^6$ | | | | | | 5 | A Medvedev | 6 | 3 | 2 | | | | | |
| Q | A Stoliarov | 6 | 5 | 7$^8$ | Q | A Stoliarov | 6 | 4 | 1 | | | | | | | | | | |
| Q | M Mirnyi | 2 | 4 | | 5 | A Medvedev | 4 | 6 | 6 | | | | | | | | | | |
| 5 | A Medvedev | 6 | 6 | | | | | | | | | | | | | | | | |

### Bottom half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals |
| 6 | M Safin | 6$^3$ | 5 | | | | | | | | | | | | | | |
| | F Santoro | 7$^7$ | 7 | | | F Santoro | 5 | 6 | 7$^8$ | | | | | | | | |
| | J Gimelstob | 6 | 6 | | | J Gimelstob | 7 | 1 | 6$^6$ | | | | | | | | |
| WC | A Cherkasov | 3 | 3 | | | | | | | | F Santoro | 3 | 4 | | | | |
| | H Arazi | 1 | 5 | | | | | | | | B Black | 6 | 6 | | | | |
| | B Black | 6 | 7 | | | B Black | 7$^7$ | 3 | | | | | | | | | |
| | G Ivanišević | 6 | 7 | | | G Ivanišević | 6$^4$ | 1$^r$ | | | | | | | | | |
| 3 | S Grosjean | 4 | 5 | | | | | | | | | | | | B Black | 6 | 6 |
| 7 | M Rosset | 3 | 6 | 6 | | | | | | | | | | | J Tarango | 3 | 2 |
| | O Ogorodov | 6 | 1 | 3 | 7 | M Rosset | 6 | 6 | | | | | | | | | |
| Q | A Derepasko | 4 | 1 | | | S Sargsian | 3 | 4 | | | | | | | | | |
| | S Sargsian | 6 | 6 | | | | | | | 7 | M Rosset | 7 | 6$^4$ | 4 | | | |
| | A Pavel | 6 | 6 | | | | | | | | J Tarango | 5 | 7$^7$ | 6 | | | |
| WC | I Kunitsyn | 2 | 2 | | | A Pavel | 3 | 5 | | | | | | | | | |
| | J Tarango | 7$^7$ | 6 | | | J Tarango | 6 | 7 | | | | | | | | | |
| 2 | V Spadea | 6$^5$ | 2 | | | | | | | | | | | | | | |