Maybe he did, maybe he did not. There is no canonical perceptive on the matter since Islam does not consider the gospels to be the preserved form of Injeel and hence does not feel it necessary to give any official explanations on any verses from it. Wherever the gospel contradicts Islamic sources (such as on the divinity and crucifixion of the Messiah) we consider the gospel to be corrupted: either its text has been altered, or its interpretation is wrong.
The essential Islamic belief regarding the ascension of Jesus عليه السلام is what is described in the following verses:
And they did not kill him, nor did they crucify him; but it appeared so to them. And indeed, those who differ over it are in doubt about it. They have no knowledge of it except the following of assumption. And they did not kill him, for certain. Rather, Allah raised him to Himself. And ever is Allah Exalted in Might and Wise.
— Quran 4:157-159
O Jesus, Son of Mary, remember My favor upon you ... and when I restrained the Children of Israel from [killing] you
— Quran 5:110
And the disbelievers planned, but Allah planned. And Allah is the best of planners. [Mention] when Allah said, "O Jesus, indeed I will take you and raise you to Myself and purify you from those who disbelieve ..."
— Quran 3:54-55
This clearly establishes that:
- The Bani Israel planned to kill Jesus but Allah saved him
- Jesus was not crucified
- Jesus was not killed
- Jesus was raised up to heavens whole - body and soul
The Quran and Hadith say nothing about a meeting with the disciples after this event. So it is possible that the gospel's account is entirely fictitious, and the disciples never met anyone.
However it is also possible that the disciples met (the real) Jesus عليه السلام after this event, as he could have briefly returned to earth to meet them and then returned to the heavens. For example this happened on the night of Isra when Muhammad ﷺ led Jesus عليه السلام and the other prophets in prayer in Bait al-Maqdis, Jerusalem (Muslim 172). So the same might have happened more than once. Hence the gospel's account could be based on some truth mixed with some falsehoods.
Ibn Kathir cites such a story in his history, and the following quote (from a different context) presents a summarized version of it:
لأن ابن جرير ذكر أن المسيح نزل من السماء بعدما رفع فوجد أمه، وامرأة أخرى يبكيان عند جذع المصلوب فأخبرهما أنه لم يقتل، وبعث الحواريين بعد
Ibn Jarir (in his Tareekh) records that Jesus descended from the sky after being raised up and found his mother and a woman weeping. And he informed them that he was not killed and then he dispatched the disciples.
— Bidayah wa'n-Nihayah
He also records this story in full under the chapter on the life of Jesus عليه السلام, and after that he comments on it as follows:
وهذا إسناد غريب عجيب، وهو أصح مما ذكره النصارى، لعنهم الله، من أن المسيح جاء إلى مريم، وهي جالسة تبكي عند جذعه، فأراها مكان المسامير من جسده، وأخبرها أن روحه رفعت، وأن جسده صلب، وهذا بهت وكذب واختلاق وتحريف وتبديل وزيادة باطلة في الإنجيل على خلاف الحق ومقتضى النقل
And the chain for this is strange, but even it is more correct than what the Christians have narrated, that Jesus came to Mary and showed her the marks of the nails on his body, and informed her that his spirit was raised and body was crucified - and this is fabrication and a lie and alteration and false addition into the Injeel.
— Bidayah wa'n-Nihayah