American Justin Gimelstob upset top-seeded Andy Murray 6-1, 7-6 in the Hall of Fame Tennis Championships semi-finals in Newport, Rhode Island on Saturday.
The eighth-seeded Gimelstob kept "The Curse of the Casino" alive at the Newport Casino, where no top seed has won the event in its 30-year history.
The 19-year-old Murray had a chance to end that streak after winning two matches on Friday to advance to the semi-finals, but never recovered after struggling throughout the first set.
Gimelstob made several spectacular saves at the net to help close out the match, staying on course for the first title of his career, which began in 1996.
Gimelstob will play Mark Philippoussis for the title on Sunday after the Australian reached his first final in three years with a 6-7, 6-2, 6-0 win over Austrian Juergen Melzer in Saturday's other semi-final.
Philippoussis will be looking for his 11th career title and his first since Shanghai in 2003, the last time he was in a final.
After dropping the first set, the big-hitting Australian dominated the rest of the match, keeping the sixth-seeded Melzer off balance and running him around the court.
In ceremonies at the Bill Talbert Stadium Court before the semi-finals, Australian Patrick Rafter and Argentina's Gabriela Sabatini were inducted to the International Tennis Hall of Fame.