# 1999 Hall of Fame Tennis Championships – Singles

Leander Paes was the defending champion, but lost in the quarterfinals to Wayne Arthurs.
Chris Woodruff won the title by defeating Kenneth Carlsen 6–7$^{(5–7)}$, 6–4, 6–4 in the final.

## Seeds

* Wayne Ferreira (second round)
* Jason Stoltenberg (first round)
* David Prinosil (second round)
* Andrew Ilie (quarterfinals)
* Sargis Sargsian (second round)
* Justin Gimelstob (first round)
* Daniel Nestor (second round)
* Sébastien Lareau (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 | Final | Final | Final | Final |
| Wayne Arthurs | 6$^4$ | 7$^7$ | 4 | | | | |
| Chris Woodruff | 7$^7$ | 6$^5$ | 6 | | | | |
| Chris Woodruff | 7$^7$ | 6$^5$ | 6 | Chris Woodruff | 6$^5$ | 6 | 6 |
| | | | | Kenneth Carlsen | 7$^7$ | 4 | 4 |
| Laurence Tieleman | 6$^6$ | 1 | | Kenneth Carlsen | 7$^7$ | 4 | 4 |
| Kenneth Carlsen | 7$^8$ | 6 | | | | | |

### 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 | Semifinals | Semifinals | Semifinals | Semifinals |
| 1/WC | W Ferreira | 6 | 6 | | | | | | | | | | | | | | |
| | M Navarra | 3 | 3 | | 1/WC | W Ferreira | 2 | 2 | | | | | | | | | |
| | L Paes | 6 | 6 | | | L Paes | 6 | 6 | | | | | | | | | |
| | N Zimonjić | 1 | 3 | | | | | | | L Paes | 7$^9$ | 6$^3$ | 3 | | | | |
| Q | C Kauffmann | 4 | 3 | | | | | | | W Arthurs | 6$^7$ | 7$^7$ | 6 | | | | |
| | W Arthurs | 6 | 6 | | | W Arthurs | 6$^6$ | 6 | 7$^7$ | | | | | | | | |
| | M Hill | 4 | 6 | 5 | 7 | D Nestor | 7$^8$ | 4 | 6$^5$ | | | | | | | | |
| 7 | D Nestor | 6 | 3 | 7 | | | | | | | | | | W Arthurs | 6$^4$ | 7$^7$ | 4 |
| 3 | D Prinosil | 6 | 6 | | | | | | | | | | | C Woodruff | 7$^7$ | 6$^5$ | 6 |
| Q | S Humphries | 4 | 4 | | 3 | D Prinosil | 2 | 4 | | | | | | | | | |
| | C Woodruff | 6 | 6 | | | C Woodruff | 6 | 6 | | | | | | | | | |
| | R Wassen | 3 | 2 | | | | | | | C Woodruff | 6 | 6 | | | | | |
| | N Godwin | 3 | 1 | | | | | | | S Pescosolido | 2 | 4 | | | | | |
| | S Pescosolido | 6 | 6 | | | S Pescosolido | 7$^7$ | 6 | | | | | | | | | |
| | M Mirnyi | 6 | 7$^7$ | | | M Mirnyi | 6$^5$ | 3 | | | | | | | | | |
| 6 | J Gimelstob | 3 | 6$^2$ | | | | | | | | | | | | | | |

### 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 | Semifinals | Semifinals | Semifinals |
| 5 | S Sargsian | 7$^7$ | 2 | 6 | | | | | | | | | | | | |
| | A Pretzsch | 6$^5$ | 6 | 4 | 5 | S Sargsian | 7$^7$ | 6$^3$ | 2 | | | | | | | |
| | L Tieleman | 6 | 6 | | | L Tieleman | 6$^4$ | 7$^7$ | 6 | | | | | | | |
| | T Ketola | 3 | 4 | | | | | | | | L Tieleman | 7$^7$ | 6 | | | |
| | C Vinck | 6 | 6 | | | | | | | 4 | A Ilie | 6$^4$ | 4 | | | |
| Q | T Blake | 4 | 0 | | | C Vinck | 4 | 5 | | | | | | | | |
| | C Caratti | 7 | 4 | 5 | 4 | A Ilie | 6 | 7 | | | | | | | | |
| 4 | A Ilie | 5 | 6 | 7 | | | | | | | | | | L Tieleman | 6$^6$ | 1 |
| 8 | S Lareau | 4 | 2 | | | | | | | | | | | K Carlsen | 7$^8$ | 6 |
| | K Carlsen | 6 | 6 | | | K Carlsen | 6 | 6 | | | | | | | | |
| WC | MV Washington | 6 | 3 | 4 | WC | J Blake | 3 | 4 | | | | | | | | |
| WC | J Blake | 1 | 6 | 6 | | | | | | | K Carlsen | 7$^7$ | 7$^7$ | | | |
| | E Ran | 3 | 3 | | | | | | | | P Wessels | 6$^4$ | 6$^5$ | | | |
| | P Wessels | 6 | 6 | | | P Wessels | 6 | 6 | | | | | | | | |
| Q | J Stark | 6 | 3 | 6 | Q | J Stark | 3 | 4 | | | | | | | | |
| 2 | J Stoltenberg | 4 | 6 | 4 | | | | | | | | | | | | |