Thomas Johansson defeated Yevgeny Kafelnikov in the final, 1–6, 6–3, 6–3 to win the men's singles tennis title at the 1999 Canadian Open.

Patrick Rafter was the defending champion, but was defeated in the quarterfinals by Nicolas Kiefer.

A champion seed is indicated in bold text while text in italics indicates the round in which that seed was eliminated. The top eight seeds received a bye to the second round.

	Semifinals							Final
	9	Nicolas Kiefer	6	1	3
	11	Thomas Johansson	4	6	6
								11	Thomas Johansson	1	6	6
								3	Yevgeny Kafelnikov	6	3	3
	3	Yevgeny Kafelnikov	6	6
	2	Andre Agassi	1	4

	First round							Second round							Third round							Quarterfinals
								1	P Rafter	6	6
		G Pozzi	5	6	3			Q	A O'Brien	0	2
	Q	A O'Brien	7	4	6										1	P Rafter	6	6
		L Paes	4	2												J Novák	3	4
		J Stoltenberg	6	6					J Stoltenberg	6	1	65
		J Novák	6	6					J Novák	3	6	77
	16	J Björkman	2	2																		1	P Rafter	3	77	64
	9	N Kiefer	6	7																		9	N Kiefer	6	65	77
		D Vacek	2	5				9	N Kiefer	6	6
		M Larsson	4	6	61				G Raoux	4	0
		G Raoux	6	4	77										9	N Kiefer	6	77
		A Ilie	6	710											8	T Haas	3	64
		M Damm	4	68					A Ilie	3	4
								8	T Haas	6	6

	First round							Second round							Third round							Quarterfinals
								4	T Henman	1	77	4
		J Courier	77	6					J Courier	6	63	6
		R Schüttler	62	2												J Courier	63	6	7
		J-M Gambill	6	6											17	W Ferreira	77	4	5
	WC	J Robichaud	0	0					J-M Gambill	5	6	68
		M Woodforde	3	7	66			17	W Ferreira	7	3	710
	17	W Ferreira	6	5	78																		J Courier	4	4
	11	T Johansson	6	6																		11	T Johansson	6	6
	WC	S Larose	2	3				11	T Johansson	7	78
		W Black	5	5				Q	M Mirnyi	5	66
	Q	M Mirnyi	7	7											11	T Johansson	77	4	6
		S Lareau	77	6												S Lareau	64	6	4
		J Gimelstob	62	1					S Lareau	4	77	6
								5	R Krajicek	6	64	4

	First round							Second round							Third round							Quarterfinals
								6	T Martin	5	6	6
		L Tieleman	6	6					L Tieleman	7	3	4
	Q	J Boruszewski	4	3											6	T Martin	6	77
	WC	B Kokavec	2	4											12	V Spadea	3	63
		J Siemerink	6	6					J Siemerink	2	2
	WC	F Niemeyer	63	4				12	V Spadea	6	6
	12	V Spadea	77	6																		6	T Martin	68	77	4
	13	G Ivanišević	4	4																		3	Y Kafelnikov	710	63	6
		B Black	6	6					B Black	7	4	66
		C Woodruff	4	6	3			Q	K Ullyett	5	6	78
	Q	K Ullyett	6	1	6										Q	K Ullyett	4	65
		A Martín	3	4											3	Y Kafelnikov	6	77
		D Nestor	6	6					D Nestor	4	4
								3	Y Kafelnikov	6	6

	First round							Second round							Third round							Quarterfinals
								LL	A Pretzsch	4	4
		F Santoro	6	7					F Santoro	6	6
		B Karbacher	2	5												F Santoro	6	6
	WC	P Gubenco	1	2												R Delgado	4	2
		R Delgado	6	6					R Delgado	6	77
		A Clément	6	2	7				A Clément	3	62
	10	T Enqvist	4	6	5																		F Santoro	0	3
	15	S Grosjean	6	1	6																	2	A Agassi	6	6
	Q	M Knowles	2	6	2			15	S Grosjean	4	3
		J Krošlák	7	5	1				M Chang	6	6
		M Chang	5	7	6											M Chang	2	5
	Q	R Reneberg	4	6	77										2	A Agassi	6	7
	Q	T Woodbridge	6	4	63			Q	R Reneberg	77	0	3
								2	A Agassi	65	6	6

• 1999 du Maurier Open draw