The question is did God ever say that Moses would enter the Promised Land?
The Background why Moses didn't enter the Promise Land
In Exodus 17:6 Moses was commanded to strike the rock to get water, which he did. In Numbers 20:8 God commanded Moses to speak to the rock to get water, but he struck it. In response to Moses disobeying God by striking the rock instead of speaking to it, God said in Numbers 20:12:
And the LORD said to Moses and Aaron, “Because you did not believe in me, to uphold me as holy in the eyes of the people of Israel, therefore you shall not bring this assembly into the land that I have given them.”
(Num. 20:12, ESV)
God confirmed this to Moses in Deuteronomy 3:23–26.
What God did tell Moses
God did tell Moses:
... I will take you to be my people, and I will be your God, and you shall know that I am the LORD your God, who has brought you out from under the burdens of the Egyptians. I will bring you into the land that I swore to give to Abraham, to Isaac, and to Jacob. I will give it to you for a possession. I am the LORD.’ ”
(Exodus 6:7–8, ESV)
When God called Moses, Moses would expect it to mean that he (Moses) would lead the children of Israel into the promise land. However, God only promised Moses he would lead the people to Mount Sinai. That is because God knew the future, but He concealed that from Moses for Moses to make his choice. Here is the call:
Then the LORD said, “I have surely seen the affliction of my people who are in Egypt and have heard their cry because of their taskmasters. I know their sufferings, and I have come down to deliver them out of the hand of the Egyptians and to bring them up out of that land to a good and broad land, a land flowing with milk and honey, to the place of the Canaanites, the Hittites, the Amorites, the Perizzites, the Hivites, and the Jebusites. And now, behold, the cry of the people of Israel has come to me, and I have also seen the oppression with which the Egyptians oppress them. Come, I will send you to Pharaoh that you may bring my people, the children of Israel, out of Egypt.” But Moses said to God, “Who am I that I should go to Pharaoh and bring the children of Israel out of Egypt?” He said, “But I will be with you, and this shall be the sign for you, that I have sent you: when you have brought the people out of Egypt, you shall serve God on this mountain.”
(Exodus 3:7–12, ESV)
Conclusion: God did not tell Moses that he (Moses himself) would enter the promise land. That would have contradicted what actually happened. However, before the striking the stone incident, Moses would have originally expected to lead the children of Israel into the promise land by implication because of God's call.