Roddick beat Nicolas Kiefer while Federer rallied to down Thomas Johansson in the semi-finals of the Toronto Masters.
Spanish tennis player Rafael Nadal is optimistic he will be ready for the Rio Olympics despite heading into next month's Games having not played a competitive match since May 27 due to a left wrist injury.
Milos Raonic of Canada will take on defending champion Novak Djokovic in the final of the Paris Masters.