| Singles | |
|---|---|
| 1999 U.S. Men's Clay Court Championships | |
| 1998 Champion |  Jim Courier |
| Champion |  Magnus Norman [1] |
| Runner-up |  Guillermo Cañas |
| Score | 6–0, 6–3 |
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.
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)| First round | Second round | Quarterfinals | Semifinals | Final [1] | ||||||||||||||||||||||||||||||
| 1 | J Stoltenberg | 6 | 65 | 6 | ||||||||||||||||||||||||||||||
| J Gimelstob | 0 | 77 | 4 | 1 | J Stoltenberg | 63 | 64 | |||||||||||||||||||||||||||
| H Gumy | 6 | 62 | 6 | H Gumy | 77 | 77 | ||||||||||||||||||||||||||||
| T Woodbridge | 3 | 77 | 4 | H Gumy | 610 | 4 | ||||||||||||||||||||||||||||
 O Stanoytchev | 7 | 0 | 4 | 7 | C Ruud | 712 | 6 | |||||||||||||||||||||||||||
| L Arnold Ker | 5 | 6 | 6 | L Arnold Ker | 6 | 63 | 2 | |||||||||||||||||||||||||||
 Á Calatrava | 4 | 2 | 7 | C Ruud | 3 | 77 | 6 | |||||||||||||||||||||||||||
| 7 | C Ruud | 6 | 6 | 7 | C Ruud | 2r | ||||||||||||||||||||||||||||
| 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 | 64 | ||||||||||||||||||||||||||||
| G Cañas | 6 | 77 | G Cañas | 6 | 77 | |||||||||||||||||||||||||||||
 S Koubek | 4 | 63 | 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 | 77 | 4 | |||||||||||||||||||||||||||
| Q |  R Cadart | 4 | 77 | 6 | Q |  M Mirnyi | 6 | 63 | 6 | |||||||||||||||||||||||||
 P Korda | 6 | 64 | 1 | Q | R Cadart | 2 | 67 | |||||||||||||||||||||||||||
| Q | M Mirnyi | 6 | 3 | 6 | Q | M Mirnyi | 6 | 79 | ||||||||||||||||||||||||||
| 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 | 63 | 0 | Q |  G Trifu | 5 | 2 | |||||||||||||||||||||||||||
| Q | G Trifu | 77 | 6 | Q | G Trifu | 6 | 6 | |||||||||||||||||||||||||||
 S Sargsian | 3 | 6 | 77 | S Sargsian | 4 | 4 | ||||||||||||||||||||||||||||
| 2 | J-M Gambill | 6 | 3 | 64 | ||||||||||||||||||||||||||||||
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The defending champion was Magnus Gustafsson, but he lost in the second round to Martín Rodríguez. The unseeded Juan Antonio Marín from Costa Rica won the singles title.