First round

Winners of the first round advanced to the quarter-finals; losers advanced to the second round.

Feb 7, 1999

Lesotho	1–0	Namibia
Teele Nts'onyana 11'

Maseru

Attendance: 12,000

Feb 20, 1999

Botswana	1–2	South Africa
Dipsy Selolwane 13'		Pollen Ndlanya 36' Alfred Phiri 39'

Gaborone

Attendance: 25,000

Apr 24, 1999

Malawi	1–2	Angola

Blantyre

Attendance: 10,000

May 9, 1999

Swaziland	3–1	Mozambique
Tholeni Nkambule 14' (pen.), 40' Dennis Masina 64'		Tomás 68' (pen.)

Somhlolo National Stadium, Lobamba

Attendance: 18,000

Second round

Losers of the first round competed for the remaining two spots for the quarter-finals.

May 22, 1999

Malawi	1–1 (2–4 pen.)	Namibia
Bimbo Tjihero 43' (o.g.)		Simon Uutoni 1'

Blantyre

Attendance: 20,000

May 28, 1999

Botswana	0–2	Mozambique
		Dario 12' Arnaldo 44'

Gaborone

Attendance: 15,000

Quarter-finals

July 4, 1999

Lesotho	0–1	Angola
		Betinho 25'

Setsoto Stadium, Maseru

Attendance: 11,000

July 18, 1999

Swaziland	1–1 (asdet) (4–3 pen.)	Zimbabwe
Bongani Mdluli 89' (pen.)		Kaitano Tembo 61'

Somhlolo National Stadium, Lobamba

Attendance: 18,000

July 31, 1999

Namibia	1–1 (asdet) (4–1 pen.)	South Africa
Johannes Hindjou 50'		Pollen Ndlanya 32'

Independence Stadium, Windhoek

Attendance: 12,000

Aug 7, 1999

Zambia	1–1 (asdet) (4–3 pen.)	Mozambique
David Siame 71'		Davies Phiri 20' (o.g.)

Independence Stadium, Lusaka

Attendance: 40,000

Semi-finals

Aug 14, 1999

Zambia	0–1	Angola
		Betinho 70'

Independence Stadium, Lusaka

Attendance: 40,000

Aug 28, 1999

Namibia	1–1 (asdet) (4–2 pen.)	Swaziland
Silvester Goraseb 67'		Dennis Masina 88'

Independence Stadium, Windhoek

Attendance: 12,000

Final

Sep 26, 1999

Angola	1–0	Namibia
Betinho 14' (pen.)

Estádio da Cidadela, Luanda

Attendance: 60,000

Oct 2, 1999

Namibia	1–1 (asdet)	Angola
Eliphas Shivute 7'		Zico 101'

Independence Stadium, Windhoek

Attendance: 12,000

1999 COSAFA Cup
Angola First title