Индепендьенте дель Валье
Diego captained the side in the first leg of the 2020 Recopa Sudamericana on 19 February 2020. The match ended in a 2–2 draw with Copa Sudamericana winners Independiente del Valle of Ecuador. Flamengo won the second leg 3–0 to secure a 5–2 aggregate victory and claim their first Recopa Sudamericana title.