Delete student submissions and allow students to re-submit

Canvas does not allow you to delete student submissions for assignments (e.g., file uploads, student annotations) nor allows you to give a specific student extra attempt(s).

This is an issue if you have restricted the number of attempts and your student provided an incomplete/wrong submission or submitted to the wrong assignment .

Students can re-submit if you increase Submission Attempts to one more than the number you permitted. This will allow the student to re-submit the assignment as a new attempt.

This increases the number of attempts for all students. To prevent other students from taking advantage of this, you can permit this for a limited period that you convey to the student(s) who need the additional attempt, then change it back once s/he has submitted.

By default, Canvas will display the latest attempt in SpeedGrader. If needed, you can select (and download) the files from the earlier attempt(s) in Speedgrader by selecting the relevant attempt from the “Submission to view” dropdown.

Alternative solutions

If the due date has passed, is to change the submission attempts, as above. However, as the due date has passed, you can assign the assignment only to the student(s) who need the extra attempt, without affecting those who already submitted on time.
You can create a separate assignment specifically for the student. Do note this will create a separate grade item in Gradebook.