The Messenger of Allah ﷺ never prayed a prayer at its latest time twice until Allah took him.
حدثنا قتيبة حدثنا الليث عن خالد بن يزيد عن سعيد بن أبي هلال عن إسحق بن عمر
ما صلى رسول الله ﷺ صلاة لوقتها الآخر مرتين حتى قبضه الله
[Hasan]. Ahmad narrated it: 6/92, hadith: 25121, from Qutayba, with the same wording. Ishaq bin Umar is majhul, Daraqutni abandoned him, and it has corroborating narrations in Hakim: 1/190, hadith 682, and elsewhere.