Two years after the military coup in Gambia, he entered first in the presidential election in 1996 as the candidate of his newly founded party UDP. He won by Jammeh 35.84 percent of the vote.
In the 2001 presidential elections, which were held on October 18, Darboe made a second attempt to win the presidency. Ousainou Darboe went as a candidate of a three-party coalition in the election, reaching 32.6 percent of the vote and was defeated again Jammeh.
Darboes party joined in 2005 with four other opposition parties together to form the National Alliance for Democracy and Development ( NADD ) and thus to prepare the campaign for the 2006 elections. This coalition broke up in 2006 but again, because they could not agree on a common candidate.
Jammeh won the 2006 presidential elections before Darboe. He was of the parties Gambia Party for Democracy and Progress ( GPDP ) and National Reconciliation Party (NRP ), because they had set up no candidate of their own. He reached this time 26.69 percent of the vote and rejected the result. In his eyes, the elections were not free and fair. Next he gave to the press that there had been extensive intimidation.