3 occurrences across the corpus

King James Version

Jeremiah 17:16

As for me, I have not hastened from being a pastor to follow thee: neither have I desired the woeful day; thou knowest: that which came out of my lips was right before thee.

OT Pseudepigrapha

The First Book of Adam and Eve 78:28

And Cain came down from the altar, his colour changed and of a woeful countenance, and came to his father and mother and told them all that had befallen him. And Adam grieved much because God had not accepted Cain's offering.

The Second Book of Adam and Eve 18:6

Then came Jared with a woeful countenance, wretched in mind and body, and sorrowful at having been separated from the bodies of his fathers.