He stood again at the 1999 election, increasing his primary vote to 56.05% and his two-party vote to 66.6%, enough to revert Port Macquarie to its traditional status as a safe National seat. Under Opposition Leader Kerry Chikarovski, on 19 April 1999 he was appointed as the Shadow Minister for Sport and Recreation and the Shadow Minister for Fisheries and Ports. Following a Shadow Cabinet reshuffle on 1 February 2000, Oakeshott lost Fisheries and Ports and took on the shadow portfolio of Gaming and Racing. However, he had become increasingly dissatisfied with the National Party, stating that he was the youngest person at most meetings he attended, and found himself in opposition to many of the party's policies.