For the person to have their 50th birthday on the same weekday as they were born, they will have to have been alive through 13 leap days. (50 extra days, one for each year, plus 13 leap days = 63: 9 weeks).

Ordinarily this will happen if they were born in the two year period immediately preceding a leap day. If they were born in the two year period immediately after a leap day they will only have lived through 12 leap days. However the situation is complicated by the fact that century years are only leap years if the number of the century is divisible by 4, so 1700, 1800 and 1900 were not leap years. So for people born in the latter half of the 1600s, 1700s or 1800s, it’s impossible to live through 13 leap days in their first 50 years. This means that the probability of the person celebrating their 50th birthday on the same weekday as they were born is roughly 5/16.

This deals with every case except for if the person was born on the 29th of February, which is difficult to account for as it is unclear exactly when they would celebrate their birthday in a non-leap year (which their 50th would certainly be).