The logic for the disk usage report is baked into SSMS and while we can't know what the RDL looks like (and if any filtering is done) I grabbed this query sent by SSMS 2016 using Profiler:
if (select convert(int,value_in_use) from sys.configurations where name = 'default trace enabled' ) = 1
begin
declare @curr_tracefilename varchar(500) ;
declare @base_tracefilename varchar(500) ;
declare @indx int ;
select @curr_tracefilename = path from sys.traces where is_default = 1 ;
set @curr_tracefilename = reverse(@curr_tracefilename);
select @indx = patindex('%\%', @curr_tracefilename) ;
set @curr_tracefilename = reverse(@curr_tracefilename) ;
set @base_tracefilename = left( @curr_tracefilename,len(@curr_tracefilename) - @indx) + '\log.trc' ;
select (dense_rank() over (order by StartTime desc))%2 as l1
, convert(int, EventClass) as EventClass
, DatabaseName
, Filename
, (Duration/1000) as Duration
, StartTime
, EndTime
, (IntegerData*8.0/1024) as ChangeInSize
from ::fn_trace_gettable( @base_tracefilename, default )
left outer join sys.databases as d on (d.name = DB_NAME())
where EventClass >= 92 and EventClass <= 95 and ServerName = @@servername and DatabaseName = db_name() and (d.create_date < EndTime)
order by StartTime desc ;
This isn't substantially different to Aaron's script and I don't see how it could return different results. It looks to me that even if the traces roll over, it will still be iterating all of them (and they wouldn't roll over 5x in the space of a few minutes or even hours of testing).