During his previous stay with Universidad de Chile in 2005 he reached the finals of the Chilean tournament, during this time he was often paired with Marcelo Salas, scoring 7 goals in the Apertura and once in the Copa Sudamericana of 2005.

In July 2009, Olivera scored the goal that would end Universidad de Chile's 5-year title drought, defeating Unión Española in the final game of the Apertura play-offs of 2009.

In August 2009, shortly after winning his first title with the Chilean club, Olivera signed a new contract with Universidad de Chile, extending his stay for another three years.

In the 2011–2012 season, Olivera accepted an offer from Al Wasl FC in Dubai to play in the UAE Football League under the supervision of the legendary Diego Maradona.

[4] On 23 January 2014, Olivera joined Argentine Primera División side Estudiantes de La Plata on a one-year loan deal.