The Messenger of Allah ﷺ never prayed a prayer at its latest time twice until Allah took him.
حدثنا قتيبة قال حدثنا ليث بن سعد عن خالد بن يزيد عن سعيد بن أبي هلال عن إسحاق بن عمر
ما صلى رسول الله ﷺ الصلاة لوقتها الآخر مرتين حتى قبضه الله عز وجل
Its isnad is daif. Ishaq bin Umar has much said against him, to the point that Daraqutni abandoned him, and Abu Hatim considered him unknown.However, the copies of Tirmidhi in our possession say, 1/328, no. 174, hasan gharib. But Tirmidhi also said, "In my view, its isnad is not connected."