# 1999 U.S. Men's Clay Court Championships – Singles

The 1999 U.S. Men's Clay Court Championships was an Association of Tennis Professionals tennis tournament held in Orlando, Florida in the United States. It was the 31st edition of the tournament and was held from April 19 to April 26. Magnus Norman won the singles title.

## Seeds

A champion seed is indicated in bold text while text in italics indicates the round in which that seed was eliminated.
* Jason Stoltenberg (second round)
* Jan-Michael Gambill (first round)
* Scott Draper (first round)
* Magnus Larsson (first round)
* Jim Courier (quarterfinals)
* Lleyton Hewitt (second round)
* Christian Ruud (semifinals, retired)
* Magnus Norman (champion)

## 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
| 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 | Final | Final | Final | Final |
| 1 | J Stoltenberg | 6 | 6$^5$ | 6 | | | | | | | | | | | | | | | | | | |
| | J Gimelstob | 0 | 7$^7$ | 4 | 1 | J Stoltenberg | 6$^3$ | 6$^4$ | | | | | | | | | | | | | | |
| | H Gumy | 6 | 6$^2$ | 6 | | H Gumy | 7$^7$ | 7$^7$ | | | | | | | | | | | | | | |
| | T Woodbridge | 3 | 7$^7$ | 4 | | | | | | | H Gumy | 6$^{10}$ | 4 | | | | | | | | | |
| | O Stanoytchev | 7 | 0 | 4 | | | | | | 7 | C Ruud | 7$^{12}$ | 6 | | | | | | | | | |
| | L Arnold Ker | 5 | 6 | 6 | | L Arnold Ker | 6 | 6$^3$ | 2 | | | | | | | | | | | | | |
| | Á Calatrava | 4 | 2 | | 7 | C Ruud | 3 | 7$^7$ | 6 | | | | | | | | | | | | | |
| 7 | C Ruud | 6 | 6 | | | | | | | | | | | | 7 | C Ruud | 2$^r$ | | | | | |
| 4 | M Larsson | 6 | 3 | 4 | | | | | | | | | | | | G Cañas | 5 | | | | | |
| | G Pozzi | 3 | 6 | 6 | | G Pozzi | 3 | 6 | 2 | | | | | | | | | | | | | |
| | A Martín | 6 | 3 | 7 | | A Martín | 6 | 3 | 6 | | | | | | | | | | | | | |
| | J Van Herck | 3 | 6 | 5 | | | | | | | A Martín | 4 | 6$^4$ | | | | | | | | | |
| | G Cañas | 6 | 7$^7$ | | | | | | | | G Cañas | 6 | 7$^7$ | | | | | | | | | |
| | S Koubek | 4 | 6$^3$ | | | G Cañas | 6 | 6 | | | | | | | | | | | | | | |
| | M Rodríguez | 3 | 4 | | 6 | L Hewitt | 2 | 2 | | | | | | | | | | | | | | |
| 6 | L Hewitt | 6 | 6 | | | | | | | | | | | | | | | | | Guillermo Cañas | 0 | 3 |
| WC/5 | J Courier | 6 | 7 | | | | | | | | | | | | | | | | 8 | Magnus Norman | 6 | 6 |
| | M Tillström | 4 | 5 | | WC/5 | J Courier | 7 | 6 | | | | | | | | | | | | | | |
| WC | A O'Brien | 5 | 3 | | | G Blanco | 5 | 4 | | | | | | | | | | | | | | |
| | G Blanco | 7 | 6 | | | | | | | WC/5 | J Courier | 3 | 7$^7$ | 4 | | | | | | | | |
| Q | R Cadart | 4 | 7$^7$ | 6 | | | | | | Q | M Mirnyi | 6 | 6$^3$ | 6 | | | | | | | | |
| | P Korda | 6 | 6$^4$ | 1 | Q | R Cadart | 2 | 6$^7$ | | | | | | | | | | | | | | |
| Q | M Mirnyi | 6 | 3 | 6 | Q | M Mirnyi | 6 | 7$^9$ | | | | | | | | | | | | | | |
| 3 | S Draper | 4 | 6 | 3 | | | | | | | | | | | Q | M Mirnyi | 2 | 1 | | | | |
| 8 | M Norman | 6 | 6 | | | | | | | | | | | | 8 | M Norman | 6 | 6 | | | | |
| Q | O Malcor | 3 | 0 | | 8 | M Norman | 6 | 6 | | | | | | | | | | | | | | |
| | L Tieleman | 3 | 0 | | | C Costa | 4 | 4 | | | | | | | | | | | | | | |
| | C Costa | 6 | 6 | | | | | | | 8 | M Norman | 7 | 6 | | | | | | | | | |
| WC | C Woodruff | 6$^3$ | 0 | | | | | | | Q | G Trifu | 5 | 2 | | | | | | | | | |
| Q | G Trifu | 7$^7$ | 6 | | Q | G Trifu | 6 | 6 | | | | | | | | | | | | | | |
| | S Sargsian | 3 | 6 | 7$^7$ | | S Sargsian | 4 | 4 | | | | | | | | | | | | | | |
| 2 | J-M Gambill | 6 | 3 | 6$^4$ | | | | | | | | | | | | | | | | | | |