Use most recent expiration date in Expired column in Members List.

my_pmpro_memberslist_expires_column.php

<?php

/**
 * Use most recent expiration date in Expired column in Members List.
 */
 function my_pmpro_memberslist_expires_column( $enddate, $user ) {
	 
	 global $wpdb;
	 
	 $filter = sanitize_text_field( $_REQUEST['l'] );
	 $old_members_filters = array( 'oldmembers', 'cancelled', 'expired' );
	 
	 if ( in_array( $filter, $old_members_filters ) ) {
		 $sql = "select enddate from {$wpdb->pmpro_memberships_users} where user_id = {$user->ID} and status != 'active' order by id desc limit 1"; 
		 $enddate = date_i18n( get_option( 'date_format' ), strtotime( $wpdb->get_var( $sql ) ) );
	 }
	 
	 return $enddate;
 }
 add_filter( 'pmpro_memberslist_expires_column', 'my_pmpro_memberslist_expires_column', 10, 2 );