How to add more than 1 user role to sub-menu pages

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The easiest way is create 2 custom capabilities and assign both to administrators, one to role coach and one to role player.

When you create your roles you do something like this:

$coach_caps = array(
  'read' => true,
  'something_else' => true,
  'can_open_coach_menu' => TRUE // this is important for your scope
);
add_role( 'coach', 'Coach', $coach_caps );

$player_caps = array(
  'read' => true,
  'something' => true,
  'can_open_player_menu' => TRUE // this is important for your scope
);
add_role( 'player', 'Player', $player_caps );

Then assign both capabilities to the administrator role:

$roles = new WP_Roles();
$roles->add_cap( 'administrator', 'can_open_coach_menu', TRUE);
$roles->add_cap( 'administrator', 'can_open_player_menu', TRUE);

Now when you add submenu pages:

// this is for administrator and coach roles
add_submenu_page( $parent, $p_title, $m_title, 'can_open_coach_menu', 'submenu1');

// this is for administrator and player roles
add_submenu_page( $parent, $p_title, $m_title, 'can_open_player_menu', 'submenu2');

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