Background: Currently, there are no diagnostic imaging-based studies that have focused specifically on the craniocervical morphology of Pomeranian dogs in relation to Chiari-like malformation and syringomyelia (CM/SM). The aims of Part I of this two-part study are to assess the intra-observer, interobserver, and intermodality reliability and agreement for various aspects of the craniocervical morphology of Pomeranians with and without CM/SM. Methods: Prospectively, Pomeranians were included that underwent both CT and MRI studies of the head and cervicothoracic vertebral column. Two observers (experienced and novice) independently performed CM and SM classifications, qualitative assessments, and quantitative measurements. The experienced observer performed these assessments twice. A third observer (experienced) performed CM and SM normal or abnormal classifications. Results: Ninety-nine (99) dogs were included. Interobserver reliability was influenced by observer experience level. For the experienced versus novice observers, substantial interobserver agreement was found for classification of SM as normal or abnormal (Cohen’s kappa = 0.63), while interobserver agreement was fair for classification of SM as normal or abnormal (Cohen’s kappa = 0.31). Interobserver, intra-observer, and intermodality reliability were variable for different measurements and assessments, and best overall for the CT-based measurements. Conclusions: Interobserver reliability and agreement results should be taken into account in the evaluation of results of future studies as well as the evaluation of imaging studies of Pomeranians presented clinically.