Serena Williams’s Next Match Will Be Friday Serena Williams’ historic U.S. Open run will continue on Friday. The 23-time Grand Slam winner has said she plans to retire after the U.S. Open – which means each match could be the last time we see her on the court. After wins in the first two rounds, Williams will face Ajla Tomljanović in Round 3 on Friday, airing on ESPN2. How far do you think Serena will go in the tournament? Who would you like her to face in the final match?