Penarol's hopes of advancing from Copa Libertadores Group Eight suffered a further setback on Tuesday night as they could only manage a 1-1 draw against Universidad de Chile in Montevideo.
The Uruguayan giants, runners-up in the tournament last year, wasted several chances before taking the lead through midfielder Nicolas Freita's superb long-range effort midway through the first half.
However, Universidad forward Junior Fernandes equalised with a powerful volley ten minutes before half-time to ensure Penarol remained rooted to the foot of the pool following defeats in their first two games last month.
In Group Three, Union Espanola and ten-man Universidad Catolica also battled out a 1-1 draw in their all-Chilean encounter.
Defender Enzo Andia headed Universidad into a 38th-minute lead only for forward Emanuel Herrera to level on the stroke of half-time for the hosts. Herrera missed a penalty, but was quick to pounce on the rebound to restore parity.
The visitors had midfielder Francisco Silva sent off for a second bookable offence when he handled the ball a minute from time.
Brazilian side Vasco da Gama came from behind to defeat Peruvian rivals Alianza Lima 3-2 at Estadio Sao Januario in Group Two.
Sebastian Charquero capitalised on sloppy home defending from a long ball to put the visitors ahead in the 17th minute, but an own goal by defender Ramos levelled things up two minutes later and then Dede completed the turnaround with a headed goal on the hour mark.
Juninho made sure of the result with an 81st-minute penalty before Walter Ibanez headed home a late consolation for Alianza.