This is most complex query. I hope this is what you are looking for.
select a.id, a.username, a.id_status,sum(a.won) won, sum(a.void) void, sum(a.lost) lost
(
select Users.id, Users.Username, User_status.id_status,
case when Analysis.status_name='Won' then 1 else 0 end won,
case when Analysis.status_name='Void' then 1 else 0 end void,
case when Analysis.status_name='Lost' then 1 else 0 end lost,
@row := case when @prevuser=Users.Username then @row + 1 else 1 end as rownum,
@prevuser:=Users.Username
FROM Users,(SELECT @row := 0, @prevuser:=null ) r
INNER JOIN User_status ON Users.User_status_name=User_status.user_status
left outer JOIN Analysis ON Users.Username=Analysis.Tipster
WHERE User_status.id_status>=3
order by Users.Username, Analysis.Tipster date
) a
where a.rownum <=20
GROUP BY a.id, a.Username, a.id_status