Benoit Paire took out Young, the No. 5 seed, 4-6, 7-6 (7-5), 6-2 in a 2-hour match.
The match turned on a seesaw second set that saw four breaks and Young ahead 5-3 in the tiebreaker. But Paire took the last four points in the tiebreaker and then won 2-of-3 break-point chances on the final set.
Earlier Guillermo Garcia-Lopez ousted the eighth-seeded Fognini 6-4, 3-6, 7-5. Garcia-Lopez converted both of his break chances in the first and third sets to advance.
Igor Andreev won 70 percent of the points on serve in a 6-3, 6-3 win over Albert Montanes in Monday's other match.
Megyn Kelly: Santa Claus and Jesus are both white men
Costly malfunction causes beer flood at Boston-area brewery