Osteochondral defects, characterized by structural compromises to articular cartilage and subchondral bone, can cause pain and lead to progressive cartilage damage and eventual osteoarthritis. Unfortunately, repairing these defects remains difficult due to the poor regenerative properties of cartilage and complex mechanical demands of the joint. As such, the field of tissue engineering aims to develop multiphasic implants that replace pathological cartilage and bone tissue and restore mechanical functionality to the joint. Recent bone physiology investigations have demonstrated that osteoclast lineage cells are inextricably involved in osteoblastic bone formation through an extensive network of anabolic signaling pathways, and so the co-delivery osteoclast and osteoblast lineage cells within scaffolds is being actively explored for bone tissue engineering purposes. However, it remains unclear how these cells can be incorporated into the design of multiphasic osteochondral scaffolds to potentially enhance subchondral bone formation and subsequent implant osseointegration. To explore this question, we examined direct surface seeding and hydrogel encapsulation as potential scaffold cellularization strategies. First, we examined how osteoclast precursor cells (OCps) and peripheral blood monocytes (PBMCs) influence early-stage bone matrix development and osteogenesis in 2D co-culture. Then, we evaluated the osteogenic potential of mesenchymal stem cells (MSCs) and PBMCs co-cultures encapsulated within a gelatin methacrylate (GelMA) hydrogel system. Our findings demonstrate that co-culturing PBMCs with MSCs in 2D cultures significantly enhanced cell proliferation, early bone matrix deposition, and the formation of cell clusters by Day 28. However, we observed no significant difference in Type I collagen (COLI) deposition between GelMA hydrogel scaffolds cultured in basal and OC conditions during the same period. Additionally, we found that the GelMA hydrogel system with MSC/PBMC co-cultures in OC conditions exhibited decreased osteogenic activity by Day 28. Collectively, our findings support the osteogenic potential of osteoclast-lineage cells in 2D culture conditions, and the potential benefits of surface-seeding for the co-delivery of osteoclast-lineage cells and MSCs in osteo-scaffolds for enhanced osteochondral regeneration and broader bone tissue engineering purposes.