Some coach of the year awards for tournaments with weird playoff systems are glitched, you might be able to get around it by assigning a specific competition to the overall table (like MLS does with Supporters' Shield) and award it to that instead.
The award names showing as blank are because you've duplicated awards but not changed the "short name" - because it often shows as what you want already, for example when duplicating USLC's "Coach of the Week" for USL1, say, you might just change the long name because that needed changing. You do have to change the "short name" at least once or it will show as blank by default. It can be changing one letter, tabbing away, and then clicking back in and changing it back (you can see on the list of "changes" for the award that it's now registered a change).