With the commencement of the Cloister government by the Retired Emperor Gofukakusa, which followed the accession of Emperor Fushimi to the throne in 1287, Tokitsugu was able to hold posts such as Innoshikken (Regent of the Cloister Government), Denso (message courier between the court's people and the Emperor), Hyojoshu (a member of Council of State) as the head of In no Kinshin (the Retired Emperor's courtier), and he was promoted to Gon Dainagon (Provisional Chief Councilor of State) in 1289, which was unusual for his family line.
弘安10年（1287年）の伏見天皇の即位に伴う後深草上皇院政開始によって一躍院近臣の筆頭として院執権、伝奏、評定衆を歴任、正応2年（1289年）には彼の家系では異例の権大納言に昇進した。