Oakland is about 74 times smaller than Timor-Leste.

Timor-Leste is approximately 14,874 sq km, while Oakland is approximately 202 sq km, making Oakland 1.36% the size of Timor-Leste.
Tip: This to-scale comparison of Timor-Leste vs. Oakland uses the Mercator projection, which distorts the size of regions near the poles.