1-dii Sebtember, 2009, kooxda Pirates ayaa soo bandhigtay waxa loo malaynayo inay yihiin kooxdii ugu horeysay ee madow ah taariikhda horyaalka. Oliver wuxuu ciyaaray saldhigga koowaad, isagoo ku biiray xiddiga labaad ee Rennie Stennett, xiddiga dhexe ee Gene Clines, xiddiga midig ee Roberto Clemente, xiddiga bidix ee Willie Stargell, qabashada Manny Sanguillén, xiddiga saddexaad ee Dave Cash, shortstop Jackie Hernández iyo tuurista Dock Ellis ee safka bilowga ah. Oliver wuxuu xilli ciyaareedkii ku soo gabagabeeyey celcelis ahaan.282, oo ay ku jiraan 31 labalaab ah (8-aad ee NL), toddobo saddex-jibbaar ah (10-aad), 10 duulimaad oo allabari ah (2-aad), iyo shan garaac oo garaac ah (oo ku wanaagsan kaalinta 9-aad ee horyaalka). Ka dib markii ay ka adkaadeen San Francisco Giants tartankii horyaalka qaranka ee 1971
Sanadkii 2011, Pirates waxay ku guuleysteen Taxanaha Adduunka, iyagoo ku garaacay Baltimore Orioles toddobo ciyaarood iyadoo Oliver uu ahaa ciyaaryahankooda dhexe ee caadiga ah.