Realizing when I'm writing that the expression I'm about to type is wrong because the types do not match still depends on my doing type checking in my head.
It seems to me that the case where typed wins is when my in-head type checker fails and I write something that is invalid. The typed language will catch that failure at compile time. The untyped won't catch it until runtime (and maybe not even then).
For the typed language, an IDE might be able to catch a mistake immediately so I don't have to wait until compilation to find it, and that immediate feedback might prevent me from writing dozens more lines with the same mistake, but even then I was using my in-head type checker to write that first mistake for the IDE to catch.