On Tuesday in Melbourne, Tommy Paul did something no American man has done in 14 years at the Australian Open: Advance to the tournament’s men’s singles semifinal round.

With the four-set victory over Ben Shelton on Day 10 of the Open, Paul also was able to advance to his first-ever Grand Slam semifinal.

Andy Roddick had been the most recent American to appear in the Open’s semis but went on to lose in that round to Roger Federer. Now, Paul will face a similar challenge when he faces Novak Djokovic, the odds-on favorite at BetMGM (-450) to win this year’s tournament.

Paul enters his match with Djokovic as the heavy underdog (+1000), and his +2000 odds are the longest of any of the field’s four remaining players. The winner of the match will face either Stefanos Tsitsipas or Karen Khachanov in the final.