The use of valid questionnaires to assess dogs' health-related quality of life (HRQoL) in veterinary practice can improve canine health outcomes and communications between veterinarians and caretakers of dogs. The Canine HRQoL Questionnaire (Canine HRQoL-Q) and the Human-Canine Bond Questionnaire (HCBQ) were developed and validated to fulfill this need. A literature review, interviews with veterinarians, and focus groups with caretakers were conducted to generate questionnaire items and develop draft questionnaires, which were piloted with caretakers to establish their content validity. Measurement properties were evaluated using data from a prospective survey study (N = 327). Draft Canine HRQoL-Q and HCBQ measures were developed, including a domain structure, items, recall period, and scale/response options. Refinements were made via iterative cognitive interviews with caretakers. When no additional revisions were indicated and content validity was established, the questionnaires were psychometrically tested. Ceiling effects were observed for all items, and factor analyses indicated that the pre-specified domains are appropriate. Internal consistency was demonstrated for the HCBQ (α = 0.79-0.86) and all but the social functioning domain of the Canine HRQoL-Q (α = 0.60). Test-retest reliability for the Canine HRQoL-Q was generally moderate-to-good (with intraclass correlation coefficients (ICCs) > 0.79). Test-retest reliability for the HCBQ was moderate (ICCs: 0.70-0.79) except for the trust domain (ICC: 0.58). Known-groups validity was demonstrated via significant differences (p < 0.05) in scores for health/bonding groups. Convergent validity was supported (r > 0.40) between all domains and the total scores for both questionnaires. The Canine HRQoL-Q and the HCBQ are valid, reliable measures of canine HRQoL for use in veterinary clinics and appear to measure related but distinct concepts that contribute to canine health and wellness.