| Men's singles | |
|---|---|
| 1999 Estoril Open | |
| Champion |  Albert Costa [1] |
| Runner-up |  Todd Martin |
| Final score | 7–6(7–4), 2–6, 6–3 |
| Draw | 32 |
| Seeds | 8 |
Alberto Berasategui was the defending champion, but lost in the first round this year.
Albert Costa won the tournament, beating Todd Martin in the final, 7–6(7–4), 2–6, 6–3.
Yevgeny Kafelnikov (first round) Todd Martin (final)
Marcelo Ríos (semifinals) Albert Costa (champion)
Gustavo Kuerten (quarterfinals) Félix Mantilla (quarterfinals) Francisco Clavet (first round) Marat Safin (first round)| Semifinals | Final [1] | ||||||||||||
 Jérôme Golmard | 4 | 4 | |||||||||||
| 4 | Albert Costa | 6 | 6 | ||||||||||
| 4 | Albert Costa | 77 | 2 | 6 | |||||||||
| 2 | Todd Martin | 64 | 6 | 3 | |||||||||
| 3 | Marcelo Ríos | 3 | 63 | ||||||||||
| 2 | Todd Martin | 6 | 77 | ||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 1 | Y Kafelnikov | 3 | 6 | 3 | |||||||||||||||||||||||
 A Pavel | 6 | 2 | 6 | A Pavel | 6 | 3 | 2 | ||||||||||||||||||||
| Q | Á López Morón | 4 | 0 |  K Alami | 3 | 6 | 6 | ||||||||||||||||||||
| K Alami | 6 | 6 | K Alami | 4 | 61 | ||||||||||||||||||||||
 F Dewulf | 2 | 1 | J Golmard | 6 | 77 | ||||||||||||||||||||||
| V Spadea | 6 | 6 | V Spadea | 3 | 2 | ||||||||||||||||||||||
| J Golmard | 77 | 77 | J Golmard | 6 | 6 | ||||||||||||||||||||||
| 7 | F Clavet | 63 | 65 | J Golmard | 4 | 4 | |||||||||||||||||||||
| 4 | A Costa | 6 | 6 | 4 | A Costa | 6 | 6 | ||||||||||||||||||||
 F Squillari | 1 | 3 | 4 | A Costa | 77 | 79 | |||||||||||||||||||||
| F Vicente | 1 | 4 | Q |  R Agénor | 65 | 67 | |||||||||||||||||||||
| Q | R Agénor | 6 | 6 | 4 | A Costa | 6 | 6 | ||||||||||||||||||||
| WC | C Costa | 6 | 2 | 64 | 6 | F Mantilla | 2 | 4 | |||||||||||||||||||
 A Medvedev | 1 | 6 | 77 | A Medvedev | 3 | 2 | |||||||||||||||||||||
 T Muster | 3 | 2 | 6 | F Mantilla | 6 | 6 | |||||||||||||||||||||
| 6 | F Mantilla | 6 | 6 | ||||||||||||||||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 5 | G Kuerten | 6 | 65 | 6 | |||||||||||||||||||||||
 JA Marín | 3 | 77 | 4 | 5 | G Kuerten | 6 | 6 | ||||||||||||||||||||
 J Novák | 77 | 6 | J Novák | 3 | 4 | ||||||||||||||||||||||
| G Blanco | 61 | 3 | 5 | G Kuerten | 4 | 3 | |||||||||||||||||||||
| Q | A Portas | 6 | 6 | 3 | M Ríos | 6 | 6 | ||||||||||||||||||||
| WC |  P Leão | 1 | 1 | Q | A Portas | 3 | 3 | ||||||||||||||||||||
| A Voinea | 6 | 4 | 2 | 3 | M Ríos | 6 | 6 | ||||||||||||||||||||
| 3 | M Ríos | 3 | 6 | 6 | 3 | M Ríos | 3 | 63 | |||||||||||||||||||
| 8 | M Safin | 66 | 7 | 3 | 2 | T Martin | 6 | 77 | |||||||||||||||||||
| H Arazi | 78 | 5 | 6 | H Arazi | 2 | 2 | |||||||||||||||||||||
| F Meligeni | 6 | 6 | F Meligeni | 6 | 6 | ||||||||||||||||||||||
| A Di Pasquale | 2 | 2 | F Meligeni | 5d | |||||||||||||||||||||||
| WC | N Marques | 6 | 3 | 6 | 2 | T Martin | 4 | ||||||||||||||||||||
| Q | G Solvès | 2 | 6 | 3 | WC | N Marques | 5 | 3 | |||||||||||||||||||
| A Berasategui | 1 | 63 | 2 | T Martin | 7 | 6 | |||||||||||||||||||||
| 2 | T Martin | 6 | 77 | ||||||||||||||||||||||||
Yevgeny Kafelnikov defeated Thomas Enqvist in the final, 4–6, 6–0, 6–3, 7–6(7–1) to win the men's singles tennis title at the 1999 Australian Open. With the win, Kafelnikov became the first Russian to win an Australian Open singles title.
Yevgeny Kafelnikov defeated Michael Stich in the final, 7–6(7–4), 7–5, 7–6(7–4) to win the men's singles tennis title at the 1996 French Open. Kafelnikov remains the most recent man to have won singles and men's doubles titles in the same major.
Pete Sampras was the two-time defending champion but lost in the quarterfinals to Paul Haarhuis.
Jim Courier was the defending champion but did not compete that year.
Nicolás Lapentti was the defending champion, but lost in the third round to Sébastien Grosjean.
Thomas Muster was the defending champion and won in the final 6–2, 6–4, 3–6, 6–3 against Richard Krajicek.
Thomas Muster was the defending champion but lost in the second round to Mark Woodforde.
Michael Chang was the defending champion and won in the final 4–6, 6–3, 6–4, 6–3 against Bohdan Ulihrach.
Marcelo Ríos was the defending champion, but lost in the third round to Todd Martin.
Carlos Moyá was the defending champion but he lost in the quarter-finals to Jérôme Golmard.
The 1999 Italian Open was a tennis tournament played on outdoor clay courts. It was the 56th edition of the Italian Open, and was part of the ATP Super 9 of the 1999 ATP Tour, and of the Tier I Series of the 1999 WTA Tour. Both the men's and the women's events took place at the Foro Italico in Rome, Italy.
Patrick Rafter was the defending champion, but lost in the final this year.
Greg Rusedski was the defending champion but lost in the second round to Albert Costa.
Andre Agassi won the title, defeating Marat Safin 7–6(7–1), 6–2, 4–6, 6–4 in the final.
Todd Martin was the defending champion but lost in the final 6–4, 7–6(7–2) against Pete Sampras.
Thomas Muster was the defending champion and won in the final 6–3, 4–6, 6–4, 6–1 against Marcelo Ríos.
Thomas Enqvist was the defending champion and won in the final 7–5, 6–4, 7–6(7–0) against Todd Martin.
Àlex Corretja was the defending champion, but lost in the second round this year.
Todd Martin was the defending champion but lost to Ivan Ljubičić in the second round.
Karol Kučera was the defending champion but lost to Àlex Corretja in the semifinals.
Jonas Björkman was the defending champion, but lost in the second round to Jason Stoltenberg.