Sydney is about 19 times bigger than Oakland.

Oakland (map shows its 131 named neighbourhoods; the area covers the whole city) is approximately 202 sq km, while Sydney (the 30 councils of metropolitan Sydney, without the Blue Mountains, Hawkesbury, Wollondilly and the Central Coast) is approximately 3,810 sq km, making Sydney 1,786% larger than Oakland.
Tip: This to-scale comparison of Oakland vs. Sydney uses the Mercator projection, which distorts the size of regions near the poles.
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