Well... I would take this a different way. I would do a Time Off object type report. For fields, I'd have User >> Name, User >> Total Entitlement, and Time Off >> End Date. Click into the column for Total Entitlement I'd select Maximum for Summarize this column by.
Then go to grouping and do a matrix grouping with User on the left, End Date (by Year) on the top. Then go to Matrix Settings and click Show Record Count and Show Value.
In my example, I just used FTE since I don't have a Total Entitlement field, but it shows you that the first Adam was allotted one 1 and only took one day. The second Adam was allotted 1 day but took 3. (And sorry about the year. We integrated with our own custom tool so we haven't used the Time Off feature since 2015. LOL!)
Hope this helps.