Left renal vein (LRV) compression resulting in signs and symptoms is commonly known as nutcracker syndrome. In nutcracker syndrome, LRV compression can result in venous tributary engorgement and symptoms such as loin pain, hematuria, and back pain. Most often, the symptoms will occur on the left side. We have described a series of patients who presented with hematuria and right flank and back pain. We performed a case series and literature review. Patient 1 was a 28-year-old woman who had initially been evaluated for concern for LRV compression. She had complaints of intermittent hematuria and right flank pain. Venography was performed, and selective venography of the renolumbar vein confirmed cross-filling across the lumbar spine to the right side. This confirmed filling across the patient's back and elicited her right flank pain. She underwent successful LRV transposition with ligation of the tributary veins, which resulted in resolution of her hematuria and right flank pain at 18 months of follow-up. Patient 2 was 39-year-old woman with microscopic hematuria, significant proteinuria, and bilateral back and flank pain, with LRV compression identified on computed tomography venography. Conventional venography with intravascular ultrasound was performed, which identified a retroaortic venous collateral vessel draining into the inferior vena cava. When this venous tributary was selected, and venography was performed, the patient experienced right-sided back pain. The nephrology workup revealed no intrinsic renal dysfunction. Thus, the patient was offered and underwent successful LRV transposition, with complete resolution of her symptoms at 12 months of follow-up. Patient 3 was a 22-year-old woman with significant right leg pain and bilateral pelvic pain and intermittent hematuria. The patient underwent venography with intravascular ultrasound that confirmed LRV compression. Significant reflux was noted in the left ovarian vein, which drained across the pelvis to the right internal iliac vein. Her left ovarian vein was dilated to 8 mm, and left ovarian vein transposition was performed. At 14 months of follow-up, the patient was doing well, with resolution of her hematuria, pelvic pain, and right leg pain. Right-sided pain is an atypical symptom that can result from LRV compression. These three cases exemplify that venous drainage pathways can vary with LRV compression and can manifest with a variety of symptoms. Clinical suspicion for LRV entrapment syndrome should include atypical presentations.