Mamluk (armour piercing) arrowheads (unfortunately I don't know the exact date, but theese were usual during the Crusades)
A crossbow bolt head and a kite-shaped flat head:
Armour piercing arrowheads from the castle of Arsuf:
A flat head from Arsuf:
Arrowheads with cross-sections from Vadum Jacob:
Arrowheads from Yoqne'am:
Painted arrow shafts from Montfort castle:
The shaft on the left is for a socketed head, which was usual among the Franks not the Mamluks.