Botswana club Jwaneng Galaxy stung Ugandan hosts Vipers by scoring direct from an 89th-minute free-kick to reach the CAF Champions League round of 32 on Saturday.
Galaxy lost the preliminary round second leg 2-1 in east Africa, but qualified 3-2 on aggregate having built a two-goal advantage at home last weekend.
The reward for the Botswana outfit is a money-spinning clash with Orlando Pirates from South Africa next month.
South African football is hugely popular in neighbouring Botswana and Pirates are likely to draw a capacity crowd when they travel for the September 15-17 first leg.
Vipers scored twice in the first half through Siraje Sentamu and Yunus Sentamu to take a two-goal lead into the break and level the tie on aggregate.
But as a penalty shootout loomed, Galaxy were awarded a free-kick just outside the penalty area and Gilberto Baruti slammed the ball into the net.
Needing to score twice to survive, 2023 Champions League group qualifiers Vipers ran out of time and fell at the first hurdle.
African Stars of Namibia, another southern Africa side hoping to cause an upset, came agonisingly close, losing to Power Dynamos of Zambia on away goals after a 2-2 aggregate draw.
Democratic Republic of Congo-born Andy Boyeli, who scored for Power in a 2-1 first-leg defeat, converted a 30th-minute penalty in mining hub Ndola to earn the Zambian outfit a 1-0 home win.
Power are the only Zambian club to have won a CAF competition, defeating BCC Lions of Nigeria in the 1991 final of the now defunct African Cup Winners Cup.
They will face Simba of Tanzania, who have reached the Champions League quarter-finals three times in the past five seasons, for a place in the group stage.
The other Tanzanian contenders, Young Africans, crushed ASAS Telecom of Djibouti 5-1 in Dar es Salaam to secure a showdown with equally experienced African campaigners Al Merrikh of Sudan.
Leading by two goals after the first leg, Yanga stretched their aggregate advantage by taking an early lead through Congolese Mpia Nzengeli and finished 7-1 overall victors.
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