John Quincy Adams lost both the electoral college and popular vote in 1824. Andrew Jackson got the largest share of each, but NO candidate won the constitutional majority of 50%. Adams won as a result of the House of Representatives election in February 1825, NOT the electoral college vote in December of 1824.
Adams Sr also lost the popular vote in his bid for re-election. could you clarify the question to make it more clear what you meant with the question pertaining to this?