The second Tadamasa of the Akasaka school carried his father's name and calling. The published sources state that 「赤坂忠正は、庄左衛門と称し同名で初二代いる」 (Akasaka Tadamasa was called Shozaemon, and there were a first and a second generation of the same name), and from a genealogy the descendant Tadatoki submitted to the shogunate in the Bunsei era they give the dates: 「初代忠正は明暦三年に歿し、二代忠正は延宝五年に歿したと記されている」 (the first Tadamasa died in Meireki 3 and the second in Enpo 5). Like all of the old Akasaka upper three generations, he left no signed work.
Two guards are recorded under his name. The first, an iron pierced with bamboo, clove and catfish on a gently squared hammered plate, is judged a work of the years when father and son worked side by side: 「二代忠正が初代と共に作鐔していた頃の傑作と推考され、赤坂透鐔全体からみても極めて優れた鐔である」 (thought to be a masterwork from the time the second Tadamasa made guards together with the first, and an exceptionally fine guard even within all Akasaka openwork). The second, pierced with the Musashino field of pampas grass, dew and a crescent moon in yin-yang openwork, the published sources assign directly: 「本作は二代赤坂忠正と鑑せられる鐔で」 (this guard is judged the second Akasaka Tadamasa), praising a refined carving that wastes no relief.
Both guards carry the construction tells the records give to the first and second generations alike, 「上部の尖った切羽台は赤坂初二代の特徴であり、小柄櫃孔にして笄櫃孔が小さいのも初二代の特徴である」 (the pointed upper is a feature of the first and second Akasaka generations, as is a smaller than the ). His hand is therefore read with his father's, and the names the second generation only where it judges a guard his. Both are designated .