MacTavish signed with the team ahead of the 1985-86 season, spending eight years as a player, winning Stanley Cups in 1987, 1988 and 1990, scoring 155 goals and 331 points across 701 games — the 10th most in franchise history. He became an alternate captain of the team in 1990, before succeeding Kevin Lowe as captain in 1992, but he would hold the title for just 148 games.

In 1994, the Oilers traded him to the New York Rangers, where he joined other ex-Oilers players in Mark Messier, Esa Tikkanen, Lowe, Glenn Anderson, and Adam Graves, winning a Stanley Cup that year. Edmonton got back Todd Marchant in the deal, who would go on to be an excellent player and a fan favourite.

Retiring after the 1996-97 season, he would return to Edmonton as an assistant coach in 1999-00, becoming head coach the following season, remaining there for eight seasons. He amassed a 301-252-47 record, helping the team reach the Stanley Cup Finals in 2006. After a few years away from the team, he would return as the senior vice-president of hockey operations in 2012-13, booking ending a stint as general manager between 2013 and 2015, before returning back upstairs through the 2018-19 campaign.

Gregg, an Edmonton native, grew up in the city attending the University of Alberta, playing there for four seasons between 1975-76 and 1978-79, later captaining team Canada in the 1980 Winter Olympics. He then played two years in Japan before signing with his hometown team in 1982. Earning a medical degree while playing for the Oilers, Gregg would play eight years for the Oilers, winning five Stanley Cups with the team in 1984, 1985, 1987, 1988 and 1990.

He spent the final year of his career in Vancouver in 1991-92, two years after they claimed him on waivers, retiring after the season and completing his residency program at the University of Alberta. Gregg later became a family physician, running a sports medicine practice in the city.

His latest endeavour has seen him become the managing director of the Edmonton Riverhawks, a summer collegiate baseball team in the West Coast League. The revitalized team has become popular in Edmonton playing at RE/MAX Field in Edmonton, where the team has set consecutive league attendance records in each of the past two years.

The Oilers Hall of Fame was launched in 2022, with the inaugural class including players and members of the organization with significant status: Al Hamilton, Wayne Gretzky, Jari Kurri, Grant Fuhr, Paul Coffey, Messier, Anderson, Lowe, Glen Sather and Rod Phillips. The first two players to be inducted beyond them that year were Ryan Smyth and Lee Fogolin, with Charlie Huddy and Doug Weight entering last year.