The St. Louis Blues surprised the hockey world — particularly the Edmonton Oilers — by extending offer sheets to restricted free agents Philip Broberg and Dylan Holloway this past week. As a result, new general manager (GM) Stan Bowman has his work cut out for him, with the seven-day deadline quickly approaching to decide whether to match the offer sheets or let the players go.
Since the 1980s, there have been nearly 44 offer sheets to restricted free agents, and with the recent ones extended to Broberg and Holloway, the Oilers have been involved in ten of those instances. With that in mind, below we’ll explore all of the other offer sheets Edmonton has been a part of.

The Rangers Extended an Offer Sheet to Geoff Courtnall in 1988

In 1988, the Oilers traded goaltender Andy Moog to Boston, receiving Bill Ranford and Geoff Courtnall in return. Courtnall played 12 regular-season games in 1988, scoring four goals and adding four assists. He also appeared in 19 playoff games, recording three assists, and earned a Stanley Cup ring as the Oilers won their fourth Cup that season.
Courtnall was a restricted free agent following the Cup win, and the New York Rangers extended an offer sheet to him in the offseason. However, at that time, the Oilers got the Washington Capitals to match the Rangers’ offer, and then they traded Courtnall to Washington for Greg Adams. That said, Adams only played in 49 games for the Oilers, whereas Courtnall went on to have an 18-year career, tallying just shy of 800 points.

Oilers Did Not Match Rangers’ Offer Sheet for Adam Graves in 1991

Forward Adam Graves played in 217 games with the Oilers, scoring 23 goals and 60 points. He was also known for playing on the ‘Kid Line’ with Joe Murphy and Martin Gelinas, and the trio was instrumental in helping Edmonton win its fifth Stanley Cup in 1990 with their aggressive forechecking, grinding, and scoring ability.
Graves was a restricted free agent after the 1990-91 season and the Rangers extended a five-year, $2.44 million offer sheet to him. The Oilers didn’t match the offer and received Troy Mallette as compensation. However, in hindsight, Edmonton should have made a better effort to keep Graves.
Mallette played in only 15 games with the Oilers, while Graves went on to play 772 games with the Rangers, scoring 280 goals and 507 points, including an impressive 52-goal campaign in 1993-94. Moreover, his jersey was raised to the rafters at Madison Square Garden in 1999.

Oilers Matched Capitals’ Offer Sheet for Dave Manson in 1992

In June 1992, the Capitals targeted restricted free agent Dave Manson, extending a three-year offer sheet with an average annual value (AAV) of $1.13 million, but the Oilers matched it. Overall, the rugged defender played in 219 games throughout three seasons in Oil Country and accumulated an impressive 570 penalty minutes. Yet, in 1994, the blueliner was eventually traded to the Winnipeg Jets in exchange for Mats Lindgren, Boris Mironov, and a first-round pick (Jason Bonsignore) and a 4th rounder.
That said, Manson returned to Edmonton in a coaching capacity and was hired as Jay Woodcroft’s assistant coach on February 10, 2022, but he was relieved of his duties last season.

The Sharks Extended an Offer Sheet to Craig Simpson in 1993

Craig Simpson played 419 regular-season games with the Oilers, scoring 185 goals and tallying 365 points and he won two Stanley Cups with the team in 1988 and 1990. Additionally, during the 1990 Cup run, he led the playoffs in scoring with 16 goals, which includes scoring the Cup-winning goal.
In 1993, the San Jose Sharks attempted to extend a three-year, $3.09 million offer sheet to Simpson who was a restricted free agent. However, the offer was invalidated because the league determined that it was improperly structured, as it consisted mainly of a signing bonus. Thereafter, there were rumours that the Buffalo Sabres would make an offer to Simpson, and as a result, the Oilers traded him to the Sabres in exchange for Jazek Cierny and a 1991 fourth-round pick (Jussi Taravinen).

Oilers Did Not Match Whalers’ Offer Sheet for Steven Rice in 1994

In 1991, Steven Rice was traded to Edmonton along with Louie DeBrusk and Bernie Nicholls as part of the deal that sent Mark Messier to the New York Rangers. Overall, Rice played in just 31 games over parts of two seasons with the Oilers.
In 1994, the Hartford Whalers extended a $1.7 million offer sheet to the restricted free agent, Rice, and the Oilers chose not to match it, and the Whalers offered Robert Kron as compensation. Edmonton declined and requested Bryan Marchment instead and the arbitrator eventually sided with the Oilers.
Additionally, Rice played four seasons with the Whalers organization, tallying 84 points. Marchment, on the other hand, played in 216 regular-season games with the Oilers over parts of four seasons, where he was a gritty presence on the blue line.

Oilers Did Not Match Blues’ Offer Sheet for Shayne Corson in 1995

In 1991, the Oilers traded Vincent Damphousse to the Montreal Canadiens in exchange for Shayne Corson, Brent Gilchrist, and Vladimir Vujtek. Overall, Corson played three seasons in Edmonton from 1992-1995, recording 137 points, and was the team’s sole representative at the All-Star Game in 1994.
After the lockout delayed the start of the 1994-1995 season, Corson was named the Oilers’ captain. However, he was stripped of the captaincy due to a series of incidents, including a clash with rookie Jason Arnott, while the team was enduring a nine-game losing streak.
In July 1995, Corson was a restricted free agent and he signed an offer sheet for five years with the Blues worth $6.95 million, which the Oilers chose not to match. As compensation, the Oilers were awarded the Blues’ first-round draft picks in both 1996 and 1997. However, Edmonton later traded these picks back to St. Louis in exchange for Mike Grier and goaltender Curtis Joseph, who were both pivotal players in the Oilers’ playoff runs in the late 90s.

Oilers Extended an Offer Sheet to Thomas Vanek in 2007

Up until this point, the Oilers’ history had been marked by other teams targeting Edmonton’s players with offer sheets. However, 2007 brought a different scenario. The Buffalo Sabres had just lost in the Eastern Conference Final, while the Oilers had missed the playoffs that season and had traded away their heart and soul player, Ryan Smyth.
Then-GM Kevin Lowe was looking to shake things up in the offseason and signed restricted free agent Thomas Vanek, who was coming off a 43-goal campaign, to a massive seven-year, $50 million offer sheet. However, before the signing, Sabres GM Darcy Regier got wind of Lowe’s intentions and warned him that he would match any offer for Vanek—which he did. In addition, Cam Lewis covered the incident before, mentioning how outraged the Sabres were:
“The Sabres were livid about Lowe’s move. Sabres General Manager Darcy Regier said it was ‘an exercise in futility,’ and Larry Quinn, a minority owner of the team, stated, ‘If there’s ever an opportunity for us to put an offer sheet on [an Edmonton] player, as long as we’re alive, we’ll be very comfortable doing that.’”
Given the enormous contract, if the Sabres had chosen not to match, they would have received the Oilers’ first-round draft picks from 2008-2011 as compensation. This would’ve likely meant that players like Taylor Hall (drafted in 2010) and Ryan Nugent-Hopkins (drafted in 2011), now the longest-serving Oiler, might never have worn an Oilers jersey. Now, in hindsight, it’s interesting to consider how different things would have been.

Oilers Extended an Offer Sheet to Dustin Penner in 2007

After missing out on Vanek in the summer of 2007, Oilers’ GM Lowe was eager to revamp his roster and set his sights on Dustin Penner from the Anaheim Ducks, just three weeks later. Penner, who had just scored 29 goals and won the Stanley Cup with the Ducks, was signed to a $21.5 million offer sheet as a restricted free agent.
Because of that, Anaheim Ducks GM Brian Burke was furious and didn’t match the offer, and the Ducks lost Penner. The two GMs had a war of words in the media, and Burke even challenged Lowe to a barn fight, and it escalated to the point where Commissioner Gary Bettman had to intervene.
As compensation for losing Penner, the Ducks received the Oilers’ first, second, and third-round picks in the 2008 NHL Draft. Anaheim used the first-round pick to trade down and select Jake Gardiner, picked Justin Schultz (who would later sign with Edmonton) with the second-rounder, and traded the third-round pick to acquire former Oiler Marc-André Bergeron.
Penner played four seasons in Edmonton, playing in 304 regular season games, where he scored 93 goals and totalled 186 points, including a career-high 63 points during the 2009-2010 season. In February 2011, the Oilers traded Penner to the Los Angeles Kings in exchange for Colten Teubert, a conditional third-round pick in 2012 (Daniil Zharkov), and a first-round pick in 2011 that became Oscar Klefbom (378 games played with Oilers), who recently retired.
After looking at the offer sheets the Oilers have been involved in throughout their history, which ones do you think they should have matched or avoided, in hindsight?