Infectious eczematoid dermatitis (IED) is defined as an acute, eczematous eruption that occurs secondary to autosensitization to purulent drainage from a primary infected site. The condition is believed to develop when bacterial products, most often the result of Staphylococcal or Streptococcal species, act as haptens and stimulate an immune response. IED typically manifests as a plaque with associated vesicles and pustules surrounding drainage from a central infectious source, or as oozing, erythema, crusting, and scaling spreading peripherally from a central infectious source. Management of IED includes both targeting the causative primary infection and suppressing the immune response producing a hypersensitivity reaction. This report details two cases. Case 1 describes a common presentation of tinea pedis. Case 2 is that of a 28 year-old-male who presented with an acute onset tender, pruritic, weeping rash after wearing boots for two straight days, and who was subsequently diagnosed and treated for IED.