Deut 28:68 was fulfilled in 70ad and 132ad...
"So this Fronto slew all those that had been seditious and robbers, who were impeached one by another; but of the young men he chose out the tallest and most beautiful, and reserved them for the triumph; (418) and as for the rest of the multitude that were above seventeen years old, he put them into bonds, and sent them to the EGYPTAIN MINES. Titus also sent a great number into the provinces, as a present to them, that they might be destroyed upon their theaters, by the sword and by the wild beasts; but those that were under seventeen years of age were sold for slaves."
(Josephus, The Wars of the Jews, Book 6, Chapter 9; 75 AD)
Following the Bar Kokhba revolt (132 AD):
"Now that Betar had been captured, everything came under Human control, while Palestine [Judah] was reduced to a desolate mound. Captives were sold into slavery in numbers too great to count. First they were brought to the grand annual market at the Terebinth-Eloh tree in Hebron, or in the words of Hyranumous, to the Tent-Ohel of Abraham near Hebron(Palestine). Each slave sold for the price of a horse. Those captives who were not sold there were brought to the market place in Azza [Gaza] which, because of the great multitudes of slaves who were sold there, was called Hadrian’s market place. And those who were still not sold there were herded into ships and WERE TAKEN TO EGYPT. Many died in transit, whether by starvation or by shipwreck, while many also were killed by cruel masters."
-- Munter; Primordia Eccl. Africanae, pp. 85f.,113.
"Innumerable was the multitude of those who were sold away as slaves. At the Annual market at Terehinth of Hebron(Palestine) they were offered fur sale in such numbers that a Jewish slave was of no more value then a horse. What could not be disposed of there was brought to Gaza and there sold or sent to Egypt, on the way to which many died of hunger, or of SHIPWRECK."
-- Emil Schurer, ” A History of the Jewish People in the Time of Jesus Christ”, Edinburgh, 1896, p.11.
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