Verses with the word sorrowful in the Old Testament (7 verses):

1 Samuel 1:15
And Hannah answered and said, No, my lord, I am a woman of a sorrowful spirit: I have drunk neither wine nor strong drink, but have poured out my soul before the LORD.

Job 6:7
The things that my soul refused to touch are as my sorrowful meat.

Psalms 69:29
But I am poor and sorrowful: let thy salvation, O God, set me up on high.

Proverbs 14:13
Even in laughter the heart is sorrowful; and the end of that mirth is heaviness.

Jeremiah 31:25
For I have satiated the weary soul, and I have replenished every sorrowful soul.

Zephaniah 3:18
I will gather them that are sorrowful for the solemn assembly, who are of thee, to whom the reproach of it was a burden.

Zechariah 9:5
Ashkelon shall see it, and fear; Gaza also shall see it, and be very sorrowful, and Ekron; for her expectation shall be ashamed; and the king shall perish from Gaza, and Ashkelon shall not be inhabited.