Chile will miss their third straight World Cup after losing 2-0 at Bolívia on Tuesday to remain last in South America's 10-team round-robin competition.
Bolivia kept their hopes alive for an inter-continental playoff spot in a bid to reach the 2026 tournament in the United States, Mexico and Canada.
The top six teams in South American qualifying will secure direct berths in the World Cup. Defending champions Argentina have already qualified.
Chile's golden generation won two Copa América titles -- in 2015 and '16 -- but are out of contention for next summer's expanded 48-team tournament.
"Sad, I am feeling bad. Never lived something like this. We have to ask people to forgive us," veteran Chile striker Alexis Sánchez said after the match. "We have to keep working. There's change already, the golden generation is buried, I am the only one left."
Bolivia scored the first with Miguel Terceros in the fifth minute and added a second in the 90th with Enzo Monteiro at the 4,150-meter high El Alto Stadium, outside La Paz.
The hosts now have 17 points to put pressure on Venezuela, who have 18 and will play later at Uruguay. Both are fighting for seventh place, which secures the inter-continental playoff spot. Sixth-place Colombia have 21 points.
Ecuador can clinch their spot with a win later at Peru. Brazil and Paraguay, who will clash in Sao Paulo, can also book their tickets if they win and Venezuela lose in Montevideo.
Also on Tuesday, Argentina host Colombia.
Bolivia's future will be decided in September at Colombia and at home against Brazil.
