[2] Initially attending Stanford University, Rostagno was on the American tennis team at the 1984 Summer Olympics, in his freshman year.

Rostagno's best performance at a Grand Slam event came at the 1988 US Open, where he reached the quarterfinals by beating Yahiya Doumbia, Martin Davis, Tim Mayotte and Ronald Agénor before being defeated by Ivan Lendl.

At Wimbledon in 1988, Rostagno lost a five-set third round match to Jimmy Connors, who at the time was ranked World No.

At the 1989 US Open, Rostagno had two straight match points in his second round encounter with Boris Becker, who won the second of those on a lucky net cord passing shot and eventually the match 1–6, 6–7, 6–3, 7–6, 6–3, en route to his lone US Open title.

He is now a practicing lawyer in Los Angeles, California, actively engaged in civil litigation in the firm that bears his name.