This example will use the WordPress Default Theme.
Read How can I have a static front page and posts display on a page called Blog?
Where it refers to Front Page think of that as your Currently Playing Page. Where it refers to Blog, think of that as your Seasons page.
For your Current Playing Page Template use this:
<?php
/*
Template Name: CurrentlyPlaying
*/
?>
<?php
get_header();
?>
<div id="content" class="narrowcolumn">
<?php
$cat=get_cat_ID('Currently Playing'); // get a category ID
query_posts ("cat=$cat&showposts=1");
?>
<?php if (have_posts()) : ?>
<?php while (have_posts()) : the_post(); ?>
<div <?php post_class() ?> id="post-<?php the_ID(); ?>">
<h2><a href="<?php the_permalink() ?>" rel="bookmark" title="Permanent Link to <?php the_title_attribute(); ?>"><?php the_title(); ?></a></h2>
<small><?php the_time('F jS, Y') ?> <!-- by <?php the_author() ?> --></small>
<div class="entry">
<?php the_content('Read the rest of this entry »'); ?>
</div>
<p class="postmetadata"><?php the_tags('Tags: ', ', ', '<br />'); ?> Posted in <?php the_category(', ') ?> | <?php edit_post_link('Edit', '', ' | '); ?> <?php comments_popup_link('No Comments »', '1 Comment »', '% Comments »'); ?></p>
</div>
<?php endwhile; ?>
<?php else : ?>
<h2 class="center">Not Found</h2>
<p class="center">Sorry, but you are looking for something that isn't here.</p>
<?php get_search_form(); ?>
<?php endif; ?>
</div>
<?php get_sidebar(); ?>
<?php get_footer(); ?>
This assumes you have a category called "Currently Playing"