Musculoskeletal symptoms are commonly reported following SARS-CoV-2 infection, with fatigue, arthralgia, and myalgia being the most common manifestations. Severe cases may include conditions like arthritis and rhabdomyolysis. Similarly, post-vaccination musculoskeletal symptoms have been documented. However, tendinopathy, particularly Achilles tendinopathy, remains underreported in both contexts. We present two cases of Achilles tendinopathy, one following SARS-CoV-2 infection and the other post-vaccination, to highlight potential musculoskeletal complications associated with COVID-19 and vaccination. In the first case, a 48-year-old male developed bilateral ankle pain eight weeks after a confirmed COVID-19 infection. The second case involves a 27-year-old male who experienced sudden, intense left Achilles tendon pain following SARS-CoV-2 vaccination. Case 1: The 48-year-old patient exhibited bilateral ankle pain and swelling, with MRI confirming Achilles enthesitis. Laboratory tests showed elevated ESR and CRP, with other parameters within normal ranges. Treatment with sulfasalazine led to significant improvement. Case 2: The 27-year-old patient demonstrates Achilles tendon rupture post-vaccination. Detailed findings and treatment outcomes were discussed to emphasize the rarity and significance of this condition. These two cases underscore the need for awareness and further research on the relatively serious musculoskeletal complications like Achilles tendinopathy following COVID-19 infection and vaccination. Enhanced medical understanding is crucial for optimizing patient care and addressing potential side effects effectively.