Nikephoros appears for the first time in Emperor Basil II's Bulgarian wars, in 999/1000, 1000/1 or 1002, depending on the source. At the time he was a "protospatharios", and along with the "patrikios" Theodorokanos, he commanded a campaign deep into Bulgarian lands. Setting out from Mosynopolis, the two generals crossed the Balkan Mountains and captured the old Bulgarian capitals of Pliska and Great Preslav, along with Little Preslav. They then plundered the Dobruja, left behind garrisons and returned to their base. It is unclear whether he was already the military governor ("strategos") of Philippopolis at the time, or was appointed to it after the successful conclusion of the campaign, as John Skylitzes reports, when Theodorokanos, who is known to have previously held the post, retired due to his advanced age.