Ryan played college hockey for the Michigan Wolverines and played on a line with Brendan Morrison during his sophomore season. He left Michigan after his sophomore season and turned pro.
Sittler was drafted by the Philadelphia Flyers in the first round (7th overall) of the 1992 NHL Entry Draft. With the selection of Ryan he and his father became the first father and son selected in the top ten in the draft's history, Darryl having been selected 8th overall in 1970 By the Toronto Maple Leafs.