As more PDS [Professional Development School] and ITP [Initial Teacher Preparation] programs move toward year-long teacher residency/co-teaching models, it becomes even more critical that we--university faculty, P-12 administrators and PDS leadership--strategically match teacher candidates and experienced teachers. How might we go about doing this very complex work of matching and building partnerships that will be inherently personal and professional, longitudinal and deep, vulnerable and supportive, between two individuals who have never met? How do we and can we match mentors and candidates in order to foster positive, professionalizing, reciprocal, and mutually-developing partnerships? How might we match individuals in ways that promote the critically transformative experiences for mentor, mentee, and pupils? We posed these questions at a Questions Session at the 2019 NAPDS [National Association for Professional Development Schools] Conference. This manuscript forwards and extends that conversation, highlighting the innovative clinical practices for mentor matching shared across multiple PDS networks.