Federer overcame wet and windy conditions on a temporary outdoor clay court in Amsterdam to beat the 159th-ranked de Bakker 6-3, 6-4, 6-4.
"On the serve, it can play tricks on you," Federer said of the gusty wind. "The ball, after you tossed it, it was moving away from you and you had to adjust the whole time. So to find a way to move the serve was pretty difficult."
Federer said the match probably wouldn't have started on the regular tennis circuit because of the rain, but he played down the conditions.
"It's OK, no problem," he said. "I mean, I'd prefer a sunny day, who wouldn't? But this is a challenge as well."
Federer's doubles partner Wawrinka had a tougher time against Haase, but won 6-3, 3-6, 6-3, 7-6 (4).
Federer and Wawrinka, the 2008 Olympic doubles champions, can wrap up the playoff Saturday by beating Haase and Jean-Julien Rojer in the doubles. Reverse singles are scheduled for Sunday.