(1) Background: The main aim of this study was to investigate the effects of different cements (Panavia V5, RelyX U200) and placement techniques (indirect ultrasonic vibration and manual method) on the bond strength of glass fiber posts in teeth with different post space preparation methods and to evaluate the failure types. (2) Methods: A total of 120 human upper central teeth were collected for the study. One week after root canal treatment, 10 mm long post space preparation was performed using post drills. Post spaces were irrigated in three different ways, namely NaOCl, NaOCl + EDTA solutions, and passive ultrasonic irrigation of NaOCl and EDTA solutions. Glass fiber posts were divided into two groups for resin cement systems, namely RelyX U200 (3M ESPE) or Panavia V5 (Kuraray Medical). Two different methods, namely the indirect ultrasonic vibration and the manual method, were applied for post placement. Then, 1.2 mm sections were taken from the middle and coronal regions of the inserted fiber posts for a push-out test. (3) Results: the Irrigation × Cement (p = 0.002), Cement × Section (p = 0.043) and Placement × Section (p = 0.049) pairwise interactions were statistically significant. (4) Conclusions: in our study, the effects of different post cavity preparations, different cement types, and different placement techniques on the bond strength of the fiber post were observed.