1999 CAF Cup
{{Infobox International Football Competition
| tourney_name = CAF Cup
| year = 1999
| other_titles =
| image =
| size =
| caption =
| country =
| dates = 14 March - 28 November
| num_teams = 30
| confederations = 1
| venues =
| cities =
| champion_other = {{flagicon|TUN}} ES Sahel
| count = 2
| second_other = {{flagicon|MAR}} Wydad AC
| matches = 57
| goals = 148
| attendance =
| top_scorer =
| player =
| updated =
| prevseason = 1998
| nextseason = 2000
}}
The 1999 CAF Cup was the eighth football club tournament season that took place for the runners-up of each African country's domestic league. It was won by ES Sahel in two-legged final victory against Wydad Casablanca.
First round
{{TwoLegStart}}
{{TwoLegResult|USM Alger|ALG|4–4 (a)|Horoya AC|GUI|2–1|2–3}}
{{TwoLegResult|Al Ahli SC (Khartoum)|SUD|2–0|Medhin|ETH|1–0|1–0}}
{{TwoLegResult|Canon Yaoundé|CMR|2–0|APR FC|RWA|2–0|0–0|var2=1962}}
{{TwoLegResult|Mumias Sugar|KEN|1–2|Ferroviário da Beira|MOZ|1–1|0–1}}
{{TwoLegResult|Zamalek SC|EGY|{{Tooltip|w/o|Walkover}}|Elite FC|BDI|—|—}}
{{TwoLegResult|Stade Tamponnaise|REU|6–1|ASF Fianarantsoa|MAD|5–1|1–0}}
{{TwoLegResult|Great Olympics|GHA|3–4|Étoile Filante|BFA|3–2|0–2}}
{{TwoLegResult|AS Vita Club|COD|8–0|Deportivo Mongomo|EQG|7–0|1–0|var1=1997}}
{{TwoLegResult|Wydad AC|MAR|3–1|Al-Ahly Benghazi|LBY|1–1|2–0|var2=1977}}
{{TwoLegResult|ASC Diaraf|SEN|4–0|Man FC|CIV|1–0|3–0}}
{{TwoLegResult|Kwara United|NGR|4–0|Young Africans|TAN|1–0|3–0}}
{{TwoLegResult|Saneamento Rangol|ANG|4–2|Police SC|BOT|3–2|1–0}}
{{TwoLegResult|ES Sahel|TUN|5–0|Centre Salif Keita|MLI|3–0|2–0}}
{{TwoLegResult|Medlaw Megbi|ERI|1–6|Express Red Eagles|UGA|1–0|0–6}}
{{TwoLegResult|Nkana FC|ZAM|8–3|Royal Leopards|SWZ|2–2|6–1}}
{{TwoLegResult|CS Sfaxien|TUN|{{Tooltip|w/o|Walkover}}|Energie Sport|BEN|—|—}}
|}
Second round
{{TwoLegStart}}
{{TwoLegResult|Al Ahli SC (Khartoum)|SUD|0–7|USM Alger|ALG|0–2|0–5}}
{{TwoLegResult|Ferroviário da Beira|MOZ|0–1|Canon Yaoundé|CMR|0–0|0–1}}
{{TwoLegResult|Stade Tamponnaise|REU|0–3|Zamalek SC|EGY|0–0|0–3}}
{{TwoLegResult|AS Vita Club|COD|2–3|Étoile Filante|BFA|1–1|1–2|var1=1997}}
{{TwoLegResult|ASC Diaraf|SEN|2–3|Wydad AC|MAR|1–1|1–2}}
{{TwoLegResult|Saneamento Rangol|ANG|{{Tooltip|w/o|Walkover}}|Kwara United|NGR|1–1|—}}
{{TwoLegResult|Express Red Eagles|UGA|2–4|ES Sahel|TUN|2–2|0–2}}
{{TwoLegResult|CS Sfaxien|TUN|4–1|Nkana FC|ZAM|4–0|0–1}}
|}
Quarter-finals
{{TwoLegStart}}
{{TwoLegResult|CS Sfaxien|TUN|4–5|ES Sahel|TUN|1–2|3–3}}
{{TwoLegResult|Kwara United|NGR|2–5|Zamalek SC|EGY|2–1|0–4}}
{{TwoLegResult|Étoile Filante|BFA|1–2|Canon Yaoundé|CMR|1–1|0–1}}
{{TwoLegResult|Wydad AC|MAR|2–2 (a)|USM Alger|ALG|1–0|1–2}}
|}
Semi-finals
{{TwoLegStart}}
{{TwoLegResult|ES Sahel|TUN|3–3 (a)|Zamalek SC|EGY|2–0|1–3}}
{{TwoLegResult|Canon Yaoundé|CMR|2–2 (5–6 p)|Wydad AC|MAR|1–1|1–1}}
|}
Final
Winners
{{winners-other|1999 African Cup Winners' Cup Winners|TUN|ES Sahel|Second}}