Background/Objectives: Sphenoid wing meningiomas are skull base meningiomas whose resection is often complicated by involvement of the optic canal, cavernous sinus, orbit, and internal carotid artery. However, prior studies use heterogeneous classification systems that may conflate tumor site of origin with patterns of extension, making comparisons by location difficult. We evaluated sphenoid wing meningiomas using an origin-based classification to assess differences in extent of resection according to tumor origin and cavernous sinus invasion. Methods: We retrospectively reviewed 39 patients who underwent resection of histopathologically confirmed sphenoid wing meningiomas at a single center between 2010 and 2024. Tumors were classified as medial or lateral according to their dominant dural attachment on MRI. An exploratory stratified analysis compared GTR rates between medial and lateral tumors according to cavernous sinus invasion status. Results: GTR was achieved in 4 of 15 medial tumors (26.7%) and 18 of 24 lateral tumors (75.0%; p = 0.007). Cavernous sinus invasion occurred in 9 of 15 medial and 2 of 24 lateral tumors. Among tumors without cavernous sinus invasion, GTR was achieved in 4 of 6 medial and 18 of 22 lateral tumors (66.7% vs. 81.8%; p = 0.58). All six events were progression after STR, with no recurrence after GTR. The 1-year recurrence-free survival after GTR and progression-free survival after less-than-GTR were 100% and 73.9%, respectively (p = 0.005). Conclusions: Medial sphenoid wing meningiomas more often involve critical skull base structures and are less likely to undergo GTR. The smaller observed difference among non-invaded tumors is hypothesis-generating because this subgroup only comprised six medial tumors.