Background: Upper extremity deep vein thrombosis (UEDVT) is uncommon but not insignificant. The current literature is limited, and the management is largely extrapolated from the treatment of lower extremity DVTs (LEDVT). Methods: A retrospective review was conducted on patients diagnosed with UEDVT at Northern Health, Victoria, Australia, between December 2010 and December 2022. Medical records were reviewed to assess baseline characteristics and treatment outcomes. The results were compared to our previously collected data for LEDVTs. Results: 137 patients with UEDVT were identified (52.6% females; median age 62 years, IQR 46–74 years). A total of 105 patients (76.6%) had at least one provoking factor at the time of diagnosis, most commonly malignancy (45.7%) and/or indwelling venous devices (58.1%). Fourteen patients (10.1%) were subsequently diagnosed with Paget–Schroetter syndrome, with nine receiving endovascular or surgical intervention. A total of 109 patients (79.6%) received limited therapeutic anticoagulation (median 3 months, IQR 1.5–6.0 months) with enoxaparin, the most common anticoagulant used. Six patients had major bleeding (5.2/100-patient-years), and seven developed clot progression while on anticoagulation (6.0/100-patient-years). Ten patients had recurrent VTE following anticoagulation cessation (4.6/100-patient-years). There were no significant differences seen in the complication rate between catheter-related UEDVT and other UEDVTs. Compared to LEDVT, UEDVT was more likely provoked with comparable complication rates. Conclusions: UEDVTs were commonly associated with a provoking factor, with indwelling catheters and/or malignancies being the most common. Interestingly, catheter-related UEDVT had comparable clot progression/recurrence and major bleeding compared to other UEDVTs and LEDVTs, which may be confounded by relatively high rates of malignancy.