Gilbert was born on 31 May 1990 in Goa. He was playing in the inter-village tournaments [1] when he was spotted and signed for I-League team Salgaocar S.C. and at the age of 16 was put in the u19's squad.[2] Gilbert stayed with the under-19 squad for three years before joining the first team for the 2010–11 I-League.[2] Speaking about his time with the youth Gilbert said "the youth development programme was excellent! My coaches really helped me in my quality of passing, ball possession, discipline, etc."[2] He made his debut for the Salgaocar first team on 7 December 2012 in the 2nd Round of the 2010-11 I-League season in Salgaocar's 4–3 victory over Chirag United in which he also managed to score his first two goals of his professional career.[2] In the sixteenth round of the I-League season Gilbert scored two more goals against ONGC which brought his tally to five that season. In the seventeenth round Gilbert scored a goal against HAL. After his first season in professional football Gilbert finished with 6 goals in 17 matches.
Olivera's 2011-12 footballing season started off great for him as he started as a normal starter for Salgaocar. He started Salgaocar's first match of the season in the 2011 Indian Federation Cup against Mumbai F.C. where they drew 0-0. He then played in his third match of the Federation Cup on 22 September 2011 and he even scored a goal as Salgaocar won 3–0 against normal I-League team Pailan Arrows.[3] Then on 29 September 2011 Olivera came on as a sub during the 2011 Indian Federation Cup Final win over East Bengal.[4] He then made his club international debut against Al-Oruba on 7 March 2012 in the 2012 AFC Cup. Salgaocar lost 0–1.[5] He then scored his first Asian and club international goal of his career against Neftchi in his second club international game of his career on 21 March 2012.[6]
On 18 November 2015, Oliveira was signed by Indian Super League side, Chennaiyin, as a replacement for Dhanpal Ganesh.[7]
