Common indications for cheek tooth extraction in the horse include dental fracture, periodontal disease, severe decay/ caries, mandibular fracture with alveolar/tooth involvement, and periapical abscess. Complications secondary to extraction of cheek teeth are prevalent. Typical complications may include retained root tip(s), collateral damage of neighboring teeth and alveolar bone, mandibular fracture non-union or delayed union, cemental ankylosis, dilacerated root(s), oroantral/oronasal fistula, palatal deviation of cheek teeth, bone sequestration, sinus involvement, alveolar plug failure, and palatine artery laceration. This paper presents a series of cases that had complications following cheek tooth extraction. Anticipation of problematic extractions, recognition of complications, and appropriate treatment will aid the clinician in managing the inevitable cheek tooth extraction complication.