Oakes was originally drafted in the 24th round of the 2006 Amateur draft by the Oakland Athletics. He spent his first three professional seasons in the A's organization. In 2008 he split time between the Stockton Ports in the A's organization and Midwest in the independent Frontier League. Oakes has a career record of 11-9 with an ERA of 4.70 in 112 games he has made no starts. Oakes has struck out 180 batters in 161 innings pitched and notched 23 saves.