should be possible,
but definitely a complex nested loop that contains date-splitting and count is needed for that. also you probably need to build a own array before you echo something.
my advise is build it at your own, or find/pay someone that can do it for you.
the only help i can give is this tip:
build a array and use this php-functions => date, strtotime, foreach, count
//to get month or year
$get_date = get_field('datefield');
$get_date_month = date('m', strtotime($get_date));
$get_date_year = date('Y', strtotime($get_date));
//build a array out of lesson, year, month and day, something like that
// $array[$lession][$year][$month][$date]
// then use a foreach loop with count on month to build your table
