1999 US Open – Boys' singles
# 1999 US Open – Boys' singles

David Nalbandian was the defending champion, but did not compete this year.

Finnish player Jarkko Nieminen defeated Danish first seed Kristian Pless in the all-Nordic final, 6–7, 6–3, 6–4.

## Seeds

* Kristian Pless (final)
* Irakli Labadze (quarterfinals)
* José Acasuso (second round)
* Danai Udomchoke (third round)
* Guillermo Coria (second round)
* Éric Prodon (first round)
* Jarkko Nieminen (champion)
* Phillip King (quarterfinals)
* Todor Enev (third round)
* Mardy Fish (quarterfinals)
* Joachim Johansson (first round)
* Nicolas Mahut (semifinals)
* Andy Roddick (first round)
* Maximillian Abel (third round)
* Levar Harper-Griffith (third round)
* Mario Ančić (second 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

| Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals | Final | Final | Final | Final | Final |
| - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| 1 | Kristian Pless | 6 | 6 | | | | | | | | | | |
| | Julien Benneteau | 2 | 4 | | | | | | | | | | |
| | Julien Benneteau | 2 | 4 | | 1 | Kristian Pless | 6 | 7 | | | | | |
| | | | | | | Dmitry Vlasov | 3 | 6 | | | | | |
| 10 | Mardy Fish | 2 | 4 | | | Dmitry Vlasov | 3 | 6 | | | | | |
| | Dmitry Vlasov | 6 | 6 | | | | | | | | | | |
| | Dmitry Vlasov | 6 | 6 | | | | | | 1 | Kristian Pless | 7 | 3 | 4 |
| | | | | | | | | | 7 | Jarkko Nieminen | 6 | 6 | 6 |
| 8 | Phillip King | 5 | 4 | | | | | | | | | | | 7 | Jarkko Nieminen | 6 | 6 | 6 |
| 12 | Nicolas Mahut | 7 | 6 | | | | | | | | | | |
| 12 | Nicolas Mahut | 7 | 6 | | 12 | Nicolas Mahut | 4 | 5 | | | | | |
| | | | | | 7 | Jarkko Nieminen | 6 | 7 | | | | | |
| 7 | Jarkko Nieminen | 5 | 6 | 6 | 7 | Jarkko Nieminen | 6 | 7 | | | | | |
| 2 | Irakli Labadze | 7 | 3 | 4 | | | | | | | | | |

### Top half

**Section 1**

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| 1 | Kristian Pless | 2 | 6 | 7 | | | | | | | | | | | | | | |
| | Roko Karanušić | 6 | 1 | 6 | 1 | K Pless | 7 | 6 | | | | | | | | | | |
| | Lee Childs | 6 | 6 | | | L Childs | 6 | 4 | | | | | | | | | | |
| | Tomer Suissa | 4 | 1 | | | | | | | 1 | K Pless | 6 | 3 | 6 | | | | |
| | Vitali Chvets | 6 | 6 | | | | | | | 15 | L Harper-Griffith | 3 | 6 | 3 | | | | |
| | Yorke Allen | 1 | 1 | | | V Chvets | 6 | 2 | 6 | | | | | | | | | |
| | Wang Yeu-tzuoo | 4 | 4 | | 15 | L Harper-Griffith | 3 | 6 | 7 | | | | | | | | | |
| 15 | Levar Harper-Griffith | 6 | 6 | | | | | | | | | | | | 1 | K Pless | 6 | 6 |
| 11 | Joachim Johansson | 3 | 7 | 3 | | | | | | | | | | | | J Benneteau | 2 | 4 |
| | Jhonnatan Medina-Álvarez | 6 | 6 | 6 | | J Medina-Álvarez | 2 | 1 | | | | | | | | | | |
| | Wong Wing-luen | 5 | 2 | | | P Hammer | 6 | 6 | | | | | | | | | | |
| | Philipp Hammer | 7 | 6 | | | | | | | | P Hammer | 6 | 1 | 1 | | | | |
| | Julien Benneteau | 7 | 6 | 6 | | | | | | | J Benneteau | 3 | 6 | 6 | | | | |
| | Timo Nieminen | 5 | 7 | 1 | | J Benneteau | 6 | 3 | 6 | | | | | | | | | |
| | Steve Berke | 3 | 6 | | 5 | G Coria | 4 | 6 | 1 | | | | | | | | | |
| 5 | Guillermo Coria | 6 | 7 | | | | | | | | | | | | | | | |

**Section 2**

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| 4 | Danai Udomchoke | 5 | 7 | 6 | | | | | | | | | | | | | | |
| | Daniel Langre | 7 | 5 | 2 | 4 | D Udomchoke | 6 | 7 | 6 | | | | | | | | | |
| | Renaud Thys | 6 | 1 | | | R Nijaki | 7 | 5 | 1 | | | | | | | | | |
| | Radosław Nijaki | 7 | 6 | | | | | | | 4 | D Udomchoke | 4 | 4 | | | | | |
| | Filip Prpic | 7 | 7 | | | | | | | 10 | M Fish | 6 | 6 | | | | | |
| | Hicham Fathi El Idrissi | 6 | 5 | | | F Prpic | 6 | 1 | 4 | | | | | | | | | |
| | Tres Davis | 1 | 6 | 4 | 10 | M Fish | 2 | 6 | 6 | | | | | | | | | |
| 10 | Mardy Fish | 6 | 2 | 6 | | | | | | | | | | | 10 | M Fish | 2 | 4 |
| 9 | Todor Enev | 6 | 6 | | | | | | | | | | | | | Dmitry Vlasov | 6 | 6 |
| | Christian-Michael Straka | 2 | 3 | | 9 | T Enev | 6 | 6 | | | | | | | | | | |
| | Stephen Nugent | 4 | 2 | | | R Ginepri | 4 | 3 | | | | | | | | | | |
| | Robby Ginepri | 6 | 6 | | | | | | | 9 | T Enev | 3 | 6 | 4 | | | | |
| | Stian Boretti | 2 | 1 | | | | | | | | Dmitry Vlasov | 6 | 0 | 6 | | | | |
| | Jean-Julien Rojer | 6 | 6 | | | J-J Rojer | 1 | 6 | 2 | | | | | | | | | |
| | Dmitry Vlasov | 7 | 6 | | | Dmitry Vlasov | 6 | 4 | 6 | | | | | | | | | |
| 6 | Éric Prodon | 6 | 4 | | | | | | | | | | | | | | | |

### Bottom half

**Section 3**

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| 8 | Phillip King | 7 | 6 | | | | | | | | | | | | | | |
| | Jonas Fröberg | 6 | 4 | | 8 | P King | 7 | 7 | | | | | | | | | |
| | Ryan Newport | 2 | 1 | | | J Peralta | 6 | 5 | | | | | | | | | |
| | Julio Peralta | 6 | 6 | | | | | | 8 | P King | 4 | 6 | 6 | | | | |
| | Boris Pašanski | 3 | 1 | | | | | | | D Gremelmayr | 6 | 0 | 0 | | | | |
| | Denis Gremelmayr | 6 | 6 | | | D Gremelmayr | 6 | 6 | | | | | | | | | |
| | Simone Amorico | 3 | 6 | | 16 | M Ančić | 4 | 2 | | | | | | | | | |
| 16 | Mario Ančić | 6 | 7 | | | | | | | | | | | 8 | P King | 5 | 4 |
| 12 | Nicolas Mahut | 6 | 6 | | | | | | | | | | | 12 | N Mahut | 7 | 6 |
| | Arnaud Segodo | 5 | 2 | | 12 | N Mahut | 6 | 6 | | | | | | | | | |
| | Lu Yen-hsun | 6 | 4 | 2 | | L Joseph | 3 | 2 | | | | | | | | | |
| | Lesley Joseph | 4 | 6 | 6 | | | | | 12 | N Mahut | 6 | 6 | | | | | |
| | Hayato Furukawa | 4 | 1 | | | | | | | D Martin | 3 | 2 | | | | | |
| | David Martin | 6 | 6 | | | D Martin | 6 | 6 | | | | | | | | | |
| | Ytai Abougzir | 7 | 1 | 4 | 3 | J Acasuso | 0 | 2 | | | | | | | | | |
| 3 | José Acasuso | 5 | 6 | 6 | | | | | | | | | | | | | |

**Section 4**

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| 7 | Jarkko Nieminen | 6 | 6 | | | | | | | | | | | | | | |
| | Phillip Harboe | 3 | 3 | | 7 | J Nieminen | 6 | 6 | | | | | | | | | |
| | John-Paul Fruttero | 6 | 6 | | | J-P Fruttero | 1 | 2 | | | | | | | | | |
| | Mohamed Mamoun | 1 | 4 | | | | | | 7 | J Nieminen | 6 | 6 | | | | | |
| | Alex Bogomolov Jr. | 6 | 6 | | | | | | 14 | M Abel | 4 | 4 | | | | | |
| | Dirk Britzen | 4 | 2 | | | A Bogomolov Jr. | 0 | 6 | | | | | | | | | |
| | Lee Radovanovich | 2 | 3 | | 14 | M Abel | 6 | 7 | | | | | | | | | |
| 14 | Maximillian Abel | 6 | 6 | | | | | | | | | | 7 | J Nieminen | 5 | 6 | 6 |
| 13 | Andy Roddick | 6 | 4 | 6 | | | | | | | | | 2 | I Labadze | 7 | 3 | 4 |
| | Scott Lipsky | 3 | 6 | 7 | | S Lipsky | 3 | 6 | | | | | | | | | |
| | Peter-John Nomdo | 7 | 6 | | | P-J Nomdo | 6 | 7 | | | | | | | | | |
| | Timothy Martin | 6 | 2 | | | | | | | P-J Nomdo | 4 | 6 | | | | | |
| | Philip Stolt | 2 | 4 | | | | | | 2 | I Labadze | 6 | 7 | | | | | |
| | Julien Cassaigne | 6 | 6 | | | J Cassaigne | 2 | 4 | | | | | | | | | |
| | Mark Hitlon | 6 | 4 | 3 | 2 | I Labadze | 6 | 6 | | | | | | | | | |
| 2 | Irakli Labadze | 4 | 6 | 6 | | | | | | | | | | | | | |
