The 1999 Betty Barclay Cup singles was the singles event of the fifteenth edition of the Betty Barclay Cup, a WTA Tier II tournament held in Hamburg, Germany and part of the European claycourt season. Martina Hingis was the reigning champion but she did not compete that year.

Venus Williams won in the final 6–0, 6–3 against Mary Pierce.

The top four seeds received a bye to the second round.

	Semifinals							Final
		Barbara Schett	6	2	4
	4	Mary Pierce	2	6	6
								4	Mary Pierce	0	3
								2	Venus Williams	6	6
	3	Arantxa Sánchez Vicario	1	3
	2	Venus Williams	6	6

	First round							Second round							Quarterfinals							Semifinals
								1	J Novotná	6	6
	Q	M Maruska	2	2					A Kremer	4	2
		A Kremer	6	6											1	J Novotná	4	3
		B Schett	3	6	77											B Schett	6	6
		R Dragomir	6	2	65				B Schett	3	6	6
		E Likhovtseva	4	1				5	N Tauziat	6	4	0
	5	N Tauziat	6	6																			B Schett	6	2	4
																						4	M Pierce	2	6	6
								4	M Pierce	6	5	7
		I Spîrlea	77	2	61				A-G Sidot	2	7	5
		A-G Sidot	65	6	77										4	M Pierce	6	6
	Q	A Barna	4	5											8	C Martínez	4	4
	WC	A Glass	6	7				WC	A Glass	6	5	1
	WC	J Abe	3	2				8	C Martínez	4	7	6
	8	C Martínez	6	6

	First round							Second round							Quarterfinals							Semifinals
	6	D Van Roost	6	6
		B Rittner	4	0				6	D Van Roost	6	5	610
		S Farina	6	6					S Farina	2	7	712
	Q	E Dementieva	3	1												S Farina	2	4
		A Fusai	63	2											3	A Sánchez Vicario	6	6
		M Sánchez Lorenzo	77	6					M Sánchez Lorenzo	3	0
								3	A Sánchez Vicario	6	6
																						3	A Sánchez Vicario	1	3
	7	A Coetzer	6	77																		2	V Williams	6	6
		V Ruano Pascual	3	64				7	A Coetzer	6	6
	Q	J Nejedly	2	5					G León García	2	1
		G León García	6	7											7	A Coetzer	4	3
		S Plischke	0	3											2	V Williams	6	6
		M Serna	6	6					M Serna	3	1
								2	V Williams	6	6

	First round							Second round							Qualifying competition
	1	Maureen Drake	6	6
	WC	Lydia Steinbach	2	3
								1	Maureen Drake	1	3
									Sandra Naćuk	6	6
		Sandra Naćuk	6	6
		Sandra Klösel	2	1
																Sandra Naćuk	3	7	3
																Anca Barna	6	5	6
		Anca Barna	1	7	6
		Aleksandra Olsza	6	5	1
									Anca Barna	6	6
								8	Larisa Neiland	3	3
		Gabriela Kučerová	3	1
	8	Larisa Neiland	6	6

	First round							Second round							Qualifying competition
	4	Elena Wagner	2	3
	WC	Vanessa Henke	6	6
								WC	Vanessa Henke	2	2
									Elena Dementieva	6	6
		Elena Dementieva	3	7	6
		Lubomira Bacheva	6	5	4
																Elena Dementieva	6	6
																Jana Kandarr	4	3
		Jana Kandarr	3	77	79
	WC	Angelika Bachmann	6	64	67
									Jana Kandarr	6	6
								6	Seda Noorlander	1	2
		Lorna Woodroffe	3	5
	6	Seda Noorlander	6	7

	First round							Second round							Qualifying competition
	7	Jana Nejedly	7	6
		Patricia Wartusch	5	4
								7	Jana Nejedly	6	6
									Sandra Dopfer	3	4
		Sandra Dopfer	6	2	6
		Pavlina Stoyanova	2	6	2
															7	Jana Nejedly	6	63	6
															3	Květa Hrdličková	2	77	2
		Miriam Schnitzer	0	0
	WC	Martina Müller	6	6
								WC	Martina Müller	3	63
								3	Květa Hrdličková	6	77
		Jasmin Wöhr	6	4	3
	3	Květa Hrdličková	2	6	6

	First round							Second round							Qualifying competition
	5	Laura Golarsa	3	5
		Olga Lugina	6	7
									Olga Lugina	6	6
									Radka Pelikánová	2	3
		Radka Pelikánová	6	61	710
		Karen Cross	3	77	68
																Olga Lugina	5	3
																Marion Maruska	7	6
		Marion Maruska	7	6
		Liezel Horn	5	2
									Marion Maruska	6	78
								2	Tatiana Panova	3	66
		Petra Begerow	77	4	3
	2	Tatiana Panova	65	6	6

• ITF tournament edition details