Introduction: Concussive and sub-concussive blows are commonly sustained during contact sports. Through a detailed neuroimaging analysis, this pilot study aimed to determine if a history of sport-related concussions exacerbated cognitive decline later in life. It was hypothesized that clinical health assessments and magnetic resonance imaging (MRI) techniques would provide insight into lasting health and well-being, structural, microstructural, and functional alterations caused by a history of concussive injuries. Materials and Methods: Twenty aging, retired Canadian Football League (rCFL) players (aged 56.9 ± 6.9) had clinical testing and MRI data acquired. Cortical thickness, voxel-wise diffusion tensor imaging (DTI), and Default Mode Network (DMN) connectivity data was collected for each subject and compared against healthy controls. Retired athlete age, playing position, and career length were also examined. Results: This study found widespread cortical thinning, significantly increased mean diffusivity, increased axial diffusivity, and both hyperactivity and hypoactivity within the DMN. Athlete age, position, and career length all influenced microstructural integrity. On average, retired athletes scored about 4 times greater depression-like and concussion-related symptoms and scored significantly lower in all health categories compared to healthy controls. Conclusions: These findings suggested that lasting signs of neurological injuries were present years after retiring from professional play.