Contradiction with Joshua 18:3
This verse speaks of the Israelites' failure to possess the land, in contrast to Caleb fully receiving Hebron as his inheritance in Joshua 14:14.
Joshua 18:3: And Joshua said unto the children of Israel, How long [are] ye slack to go to possess the land, which the LORD God of your fathers hath given you?
Contradiction with Hebrews 4:8-9
These verses suggest that Joshua did not give complete rest, contradicting the complete rest implied for Caleb's inheritance in Joshua 14:14.
Hebrews 4:8-9: For if Jesus had given them rest, then would he not afterward have spoken of another day. [Jesus: that is, Joshua]
Contradiction with Judges 1:21
This verse notes the Jebusites dwelling with the children of Benjamin in Jerusalem, contrary to the idea of complete possession seen in Caleb's inheritance in Joshua 14:14.
Judges 1:21: And the children of Benjamin did not drive out the Jebusites that inhabited Jerusalem; but the Jebusites dwell with the children of Benjamin in Jerusalem unto this day.
Contradiction with Judges 1:27
There is mention that some tribes could not drive out inhabitants, contrasting with Caleb who fully possessed his land as stated in Joshua 14:14.
Judges 1:27: Neither did Manasseh drive out [the inhabitants of] Bethshean and her towns, nor Taanach and her towns, nor the inhabitants of Dor and her towns, nor the inhabitants of Ibleam and her towns, nor the inhabitants of Megiddo and her towns: but the Canaanites would dwell in that land.
Contradiction with Hebrews 11:39-40
Suggests that none received the full promise, which contradicts Caleb receiving his inheritance fully as implied in Joshua 14:14.
Hebrews 11:39-40: And these all, having obtained a good report through faith, received not the promise: