We have no meanings for "doleful day" in our records yet.
1 God grant we never live to see that doleful day .
2 Therefore I will e'en begin at that most doleful day .
3 Alas that ever I should see this doleful day .
4 My teenage years were miserable enough, but Sundays were the most doleful day of all.
5 Thus did the vision leave me, and many a doleful day succeeded to the parting moment.
6 This has been a doleful day for me.
7 As the sun was setting on that doleful day , Company A was ordered forward to the skirmish-line.
8 A watery Sabbath means a doleful day , and 'A watery Sabbath it is,' he replied with feeling.
9 As time goes on, he realises keenly what a doleful day it was for him when that other died.
10 Alas that ever I should see this doleful day , for now, said Arthur, I am come to mine end.
12 But I thought you lost that serious little girl on the doleful day when she heard you say that you loved me best.
13 A mystery has ever hung and ever must continue to hang, over the fate of King Roderick, in that dark and doleful day of Spain.
14 Their visit to Dunbarton was all happiness and reparation for the doleful days at Bennington.
15 'If that doleful day should come, while Duncan Macwheeble had a boddle it should be Miss Rose's.
16 'Alas,' said the king, 'that ever I should see this doleful day , for now is my end come.
Grammar, pronunciation and more
This collocation consists of: Doleful day through the time
Doleful day across language varieties