It fell short of the two-thirds majority needed to overturn President Donald Trump’s veto, used to override resolutions passed by both chambers of Congress preventing the sale.
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Mr Trump argued that blocking the sale would weaken US global competitiveness.
However, a number of lawmakers – including some Senate Republicans – said there was no legitimate reason to bypass Congress.
In Monday’s first vote, five Republicans voted to override the president, siding with their Democrat colleagues 45-40. Fifteen senators abstained.
Two further votes had similar margins.
The Trump administration announced in May that it was proceeding with the sale of the weapons to Saudi Arabia and the United Arab Emirates.
Mr Trump issued a national emergency declaration in order to push through the sale.
He suggested that barring it could prolong the conflict in Yemen and that “without precision-guided munitions, more – not fewer – civilians are likely to become casualties”.
The president also insisted that Saudi Arabia and the United Arab Emirates were a “bulwark against the malign activities of Iran and its proxies in the region”.
Tensions between the US and Iran have soared since the US pulled out of a landmark nuclear deal last year and reimposed sanctions.
Public information on Saudi Arabia’s military spending is limited, but it is estimated to be the world’s largest importer of weapons and the biggest military spender in the Middle East.
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