The 1999 Waldbaum's Hamlet Cup was a men's tennis tournament played on Hard courts in Long Island, United States that was part of the International Series of the 1999 ATP Tour. It was the nineteenth edition of the tournament and was held from 23–29 August 1999.

Patrick Rafter was the defending champion, but did not compete this year.

Magnus Norman won the title by defeating Àlex Corretja 7–6^(7–4), 4–6, 6–3 in the final.^[2]

Champion seeds are indicated in bold text while text in italics indicates the round in which those seeds were eliminated.

	Semifinals							Final[1]
		Magnus Norman	7	6	6
		Jason Stoltenberg	63	7	3
									Magnus Norman	7	4	6
								2/WC	Àlex Corretja	64	6	3
		Daniel Vacek	4	1
	2/WC	Àlex Corretja	6	6

	First round							Second round							Quarterfinals							Semifinals
	1	Y Kafelnikov	6	6
	Q	E Taino	3	4				1	Y Kafelnikov	7	6
		F Santoro	3	6	7				F Santoro	66	0
	Q	B Karbacher	6	3	64										1	Y Kafelnikov	6	3	1
		M Norman	6	6												M Norman	3	6	6
		S Koubek	4	2					M Norman	6	6
	LL	M Puerta	6	6				LL	M Puerta	3	3
	8	A Costa	4	1																			M Norman	7	6	6
		F Meligeni	61	7	6																		J Stoltenberg	63	7	3
	3/WC	C Moyá	7	62	3				F Meligeni	4	1
		J Stoltenberg	6	6					J Stoltenberg	6	6
		F Vicente	2	4												J Stoltenberg	w/o
		Y El Aynaoui	7	6											6	T Johansson
		F Clavet	5	1					Y El Aynaoui	4	63
	6	T Johansson	5	6	6			6	T Johansson	6	7
		M Zabaleta	7	4	3

	First round							Second round							Quarterfinals							Semifinals
	5/WC	R Krajicek	6	6
		J-M Gambill	4	3				5/WC	R Krajicek	3	4
		B Ulihrach	1	6	6				B Ulihrach	6	6
		J Novák	6	3	2											B Ulihrach	2	3
		C Ruud	6	6												D Vacek	6	6
		J Siemerink	3	3					C Ruud	3	3
		D Vacek	6	6					D Vacek	6	6
	Q	K Kim	4	2																			D Vacek	4	1
	7	T Enqvist	4	7	6																	2/WC	Àlex Corretja	6	6
		M Larsson	6	63	1			7	T Enqvist	6	6
		G Ivanišević	6	6					G Ivanišević	4	2
		A Di Pasquale	2	3											7	T Enqvist	68	6	61
	Q	M Damm	6	6											2/WC	Àlex Corretja	7	2	7
		A Medvedev	1	4				Q	M Damm	1	6	0
	2/WC	À Corretja	64	6	6			2/WC	Àlex Corretja	6	3	6
		M Rosset	7	3	4

1. Mariano Puerta

	First round							Second round							Qualifying competition
	1	Mariano Puerta	6	7
		Oren Motevassel	2	5
								1	Mariano Puerta	6	7
									Martin Lee	4	5
		Martin Lee	6	6
	WC	Kristian Pless	2	3
															1	Mariano Puerta	5r
																Kevin Kim	6
		Arvind Parmar	7	6	2
		Luke Milligan	5	7	6
									Luke Milligan	3	1
									Kevin Kim	6	6
		Kevin Kim	1	6	6
	7	Nicolás Massú	6	3	2

	First round							Second round							Qualifying competition
	2	Bernd Karbacher	6	1	7
		Lior Mor	4	6	6
								2	Bernd Karbacher	6	7
									Miles Maclagan	1	5
		Miles Maclagan	6	3	6
		Frédéric Niemeyer	2	6	2
															2	Bernd Karbacher	6	6
																Julien Boutter	3	4
		Taylor Dent	6	3
		Julien Boutter	7	6
									Julien Boutter	7	4	6
								8	Tomáš Zíb	6	6	3
		Ofer Sela	2	6	3
	8	Tomáš Zíb	6	3	6

	First round							Second round							Qualifying competition
	3	Roger Federer	6	3	7
	WC	Todd Meringoff	4	6	6
								3	Roger Federer	1	4
								WC	Eric Taino	6	6
	WC	Eric Taino	6	6
		Alexandre Simoni	3	3
															WC	Eric Taino	6	7
															WC	Fernando González	4	6
		Damien Roberts	3	2
		Timothy Aerts	6	6
									Timothy Aerts	2	6
								WC	Fernando González	6	7
	WC	Fernando González	3	6	7
	6	Jacobo Díaz	6	0	6

	First round							Second round							Qualifying competition
	4	Martin Damm	6	7
		Mark Draper	4	6
								4	Martin Damm	6	6
									Marc-Kevin Goellner	2	2
		Marc-Kevin Goellner	6	6
		Scott Draper	4	4
															4	Martin Damm	6	6
															5	Wayne Black	0	2
		Lionel Roux	6	6
		Danai Udomchoke	4	2
									Lionel Roux	4	6
								5	Wayne Black	6	7
		Eyal Ran	3	0r
	5	Wayne Black	6	3

• Official results archive (ATP)
• Official results archive (ITF)