Hundreds of protestors threw stones at unarmed police and set fire to tyres and rubbish piles as settlers were forced out of their homes in the unauthorised outpost in Amona.
Most of the Amona settlers stayed inside their homes after erecting makeshift barriers in front of their doors and vowing passive resistance to eviction.
"A Jew doesn't evict a Jew," the protesters chanted.
Demonstrators were arrested and some police officers were injured.
Around 330 Israeli settlers have lived in Amona, the largest of scores of outposts built in the West Bank without Israeli authorisation.
Israel's Supreme Court ruled in 2014 that Amona must be demolished because it was built on privately-owned Palestinian land.
It set February 8 as the final date for its destruction.
While Palestinian land-owners like Issa Zayed may get their land back, they are not necessarily happy with the process carried out to do so.
"They leave this settlement without preparing nearby Palestian lands to transfer the settlers. This is no solution. We want them to leave all our lands for good not to move their homes from Issa's land to Mohammad's. We want to be able to access our land and use it again."
Politician Oren Hazan, from Israel's ruling Likud party, says he hopes force doesn't come into play.
"Actually this morning throws me back straight to the days of the disengagement from Gaza Strip. The days of those photos, those crazy pictures of soldiers and police officers that evacuate their brothers and sisters. I hope that this day will end without violence. I call everybody to act with patience, we need to remember that we are brothers and sisters."
Meanwhile the Israeli government has announced the creation of 3,000 new Israeli homes in the West Bank.
It's the third such declaration in the 11 days since US President Donald Trump took office.
President Trump has indivated he is more sympathetic towards such projects than his predecessor, Barack Obama.
Hanan Ashrawi, an executive committee member of the Palestinian Liberation Organisation, says the construction of more Israeli homes may signal the end of the two-state solution for peace.
"This latest frenzy of settlement activities within less than two weeks of the Trump adminstration taking office is very clearly a signal to the rest of the world to say that they have American approval and that Israel is very busy creating facts on the ground to prevent the establishment a viable Palestinian state and therefore to destroy the chances of peace."
But former Israeli Justice Minister Yossi Beilin has told AlJazeera he is confident it will not set back peace efforts..
"It is very problematic that the American adminstration is totally indifferent to such a decision but if you ask me if this is something that is going to prevent us from implementing in the future a two-state solution, no, my answer is not because the worst case scenario what will be done is to put at least a significant part of the settlements under the future Palestinian state so the Israeli settlers who would wish to stay there will do it as Israeli citizens but as Palestinian residents who obey the Palestinian law."
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