The 19-year-old, who was selected in the first round (No. 14) of the 2020 NHL Draft, is expected to need three months to recover. The Oilers open the regular season Oct. 13 at home against the Vancouver Canucks.
Holloway, who signed a three-year, entry-level contract April 16 after completing his sophomore season at the University of Wisconsin, was expected to participate in Oilers rookie camp, which began Wednesday.
"It's not good news, but he's going to deal with it," Edmonton general manager Ken Holland said Wednesday. "He seems to be a very motivated athlete, very intense, very focused, so I'm optimistic as we get a couple of months down the road he's going to push hard to get back as quickly as possible."
Holloway had surgery for a wrist fracture March 29, three days after Wisconsin was eliminated from the NCAA Division I men's ice hockey tournament and was expected to need four weeks to recover. During the recovery, Oilers medical staff determined he would need another surgery.
"The scaphoid bone is a bone that takes a long time to heal, because it's a part of the body where there is very little blood flow," Holland said. "Over the course of June, July and August, Dylan would come up here on a regular basis to Edmonton, we'd have pictures taken and he'd seen our team doctors. The pictures showed it was healing very, very slowly, and we put him on a bone stimulator and we made the decision in the last couple of weeks that he would have surgery again."
Holloway was fifth among NCAA players with 35 points (11 goals, 24 assists) in 23 games last season. He scored two points (one goal, one assist) in six games to help Canada finish second at the 2021 IIHF World Junior Championship.
"It's not 100 percent right yet," Holloway said after he signed. "I don't want to rush anything. It is an injury that if I don't let it heal right away, or heal properly, it will affect my hand and my wrist for the rest of my life pretty much."
Holland said, "I'm very optimistic we're going to get Dylan healthy. He's 19 years of age, he's going to have a long career, but certainly right now it's a major disappointment. He's a young player that had a tremendous college year last [season], he played on Canada's World Junior team, he can play left wing or center … he's physically strong (6-foot-1, 203 pounds), so we were excited."
NHL.com independent correspondent Derek Van Diest contributed to this report