CAF Champions League holders Esperance stumbled at the first hurdle at the FIFA Club World Cup after losing 1-0 to Al Hilal on Saturday evening.
Former Swansea City striker Bafetembi Gomis got the game's only goal in the 73rd minute, although Hilal did finish the game with 10 men after Mohammed Kanoo picked up a second booking in the 85th minute.
Hilal will now face South American champions Flamengo in Tuesday's semi-final
Monterrey advanced to the semi-finals of the Club World Cp after defeating Al Sadd 3-2 at the Jassim Bin Hamad Stadium.
Leionel Vangioni, Rogerio Funes Mori and Carlos Rodriguez managed to find the back of the net for the Liga MX club.
2019 Africa Cup of Nations winner Baghdad Bounedjah and Abdelkarim Hassan netted for Al Sadd, but Monterrey held on for vitory.
The Liga MX outfit will now face European champions Liverpool in the second semi-final on Wednesday.