A ruptured Baker’s cyst is a presentation that can mimic deep vein thrombosis (DVT) or acute thrombophlebitis. It can complicate further with infection or compartment syndrome. Deep vein thrombosis (DVT) and Baker's cyst complicated by rupture present similar symptoms: acute pain and inflammation in the calf. We present 3 cases of ruptured Baker’s cyst presented to Department of Orthopaedics at SGRRIM&HS, Dehradun and its surgical management. Differential diagnosis is must and requires information from Doppler ultrasound imaging and for confirmation MRI because treating suspected DVT with therapeutic doses of low molecular weight heparins (LMWHs) can cause major bleeding and worsen the prognosis of complicated Baker's cyst.