Better way to extract country wise player list from html file using regex
Regular expressions is not the right tool when it comes to parsing HTML. There are specialized HTML parsers that would do a better job resulting into a more robust and less fragile solution. 

Just to name a few problems that exists in your current approach:


what if there are more than two players for a country
what if there are 0 players for a country
what if a country name contains a space or a single quote
what if a player's name consists of more than two words or contains a single quote
what if there are newlines after the opening or before the closing li tag


Instead, you may, for instance, use BeautifulSoup library:

from bs4 import BeautifulSoup


with open('playerlist.html', 'r') as input_file:
    soup = BeautifulSoup(input_file, "html.parser")


for country in soup.select("ul &gt; li"):
    country_name = country.find(text=True, recursive=False).strip()
    players = [player.get_text(strip=True) for player in country.select("ol &gt; li")]

    print('{country} - {players}'.format(country=country_name,
                                         players=', '.join(players)))