Keep in mind the most painful seasons are not necessarily the years in which the team had the worst record. Wins and losses are a factor, but sometimes a quick playoff exit after a season that created high expectations can also be a very disappointing type of campaign. A combination of expectations, performance and playoff performance (if any) are used to determine these rankings.
Feel free to comment on this list and mention any other seasons you feel belong here. As always, indicate why you feel the way you do.
After making the playoffs and even pulling off a first-round upset the previous season, the Sharks fell back to earth in 1995-96 by finishing seventh in their division and 13th in the Western Conference. San Jose's record fell to 20-55-7 and they missed the postseason.
Once again, San Jose was last in the league in goals allowed, permitting opponents to score 357 times over the course of the season. The Sharks also had the worst penalty kill in the league with a 76.57 percent kill rate.
The Sharks started the season by going 0-7-4 and never really recovered. They were 1-14-4 after their first 19 games.
Owen Nolan led the Sharks in goals with 29 while Craig Janney had a club-best 62 points. The top netminder was Chris Terreri.
At the end of the season, coach Kevin Constantine was let go.
The 1995-96 season made our list because the team was so disappointing after a promising playoff run the year before, dashing hopes that the franchise was ready to be competitive.
Jonathan Cheechoo was a big part of the Sharks' regular-season success in 2006-07.
The Sharks were 51-26-5 in 2006-07. So why does this season make our list? After a very successful regular season, which included a torrid 20-7-0 start, the Sharks were bumped out of the playoffs in the second round by the Detroit Red Wings.
General manager Doug Wilson was all in, making deals at the trade deadline to add players like Bill Guerin and Craig Rivet to bolster the playoff run. But in the end, it was another disappointing postseason performance for Team Teal and coach Ron Wilson.
Jonathan Cheechoo led the Sharks with 37 goals while Joe Thornton had an outstanding campaign, finishing with 92 assists and 114 points.
Four rookies made large impacts on this club: Ryane Clowe, Marc-Edouard Vlasic, Joe Pavelski and Matt Carle.
Evgeni Nabokov and Vesa Toskala split time in goal, but it was Nabokov who got the call in the playoffs.
The loss to Detroit was a bitter disappointment and had many experts questioning if the Sharks had what it takes to win the franchise's first Stanley Cup.
Teemu Selanne led the Sharks in goals and points in 2002-03.
After winning the Pacific Division in 2001-02, the Sharks fell to earth with a resounding thud the following season and finished with a 28-37-9 record. That placed them fifth in the division and 14th in the Western Conference. Needless to say, San Jose did not qualify for the playoffs.
The disappointing campaign resulted in changes being made both on the roster and behind the bench. By the end of November, coach Darryl Sutter was fired with the team struggling at 8-12-2-2. Ron Wilson took over, but he too was unable to right the ship.
Before the season was over, team captain Owen Nolan was also gone after general manager Dean Lombardi traded him to Toronto. Lombardi would also be gone before the start of the next season, replaced by Doug Wilson.
Teemu Selanne, Patrick Marleau and Marco Sturm all tied for the club lead in goals scored with 28 while Selanne led the team with 64 points.
The Sharks would improve the following season, but 2002-03 has to be remembered as a painful season in the franchise's history.
1992-93 was the second season in the history of the Sharks franchise, and record-wise, it was the worst in team history.
San Jose finished with an 11-71-2 record, which included a horrific 3-38-1 road mark. The 71 losses was a new NHL record.
The season was full of losing streaks. Team Teal won their season opener against the Winnipeg Jets and then lost their next nine games. There were also a pair of 13-game losing streaks during the season. But the worst slump of all started on January 4, 1993, in Montreal, and didn't end until Valentine's Day when the Sharks beat the Jets 3-2 in Winnipeg. The Sharks lost 17 straight games and went 0-13-1 for the month of January that season.
San Jose allowed the most goals in the league (414) and was shut out six times, also the most in the league.
There were some highlights for coach George Kingston's beleaguered club even if they were few and far between. Goalie Arturs Irbe recorded the first shutout in franchise history on November 17, 1992, in a 6-0 win over the Kings.
Rob Gaudreau recorded the first hat trick in Sharks' history this season as well when he scored three times in a 7-5 loss to the Hartford Whalers on December 3.
Veteran center Kelly Kisio led the team in goals, assists and points. The captain was defenseman (and current general manager) Doug Wilson.
There weren't high expectations for the 1992-93 Sharks, but they had one of the worst seasons in NHL history and tested the patience of the fans at the old Cow Palace throughout this frustrating campaign.
The Sharks won the Presidents' Trophy in 2008-09 after a 53-18-11 season, good for 117 points.
New head coach Todd McLellan arrived from the Red Wings' organization and was determined to take Team Teal to the next level, which meant playoff success.
The team got off to a strong start with a 20-3-1 mark by the end of November and they never looked back.
The Sharks had scoring depth, as six players topped the 20-goal mark led by Patrick Marleau's 38 tallies. Joe Thornton led the team with 86 points while newly acquired defenseman Dan Boyle led all defensemen with 57 points in 77 games.
Starting goalie Evgeni Nabokov had another strong season that included seven shutouts and 41 wins.
But once again, the Sharks disappointed their fans and themselves by making a quick playoff exit. The Anaheim Ducks upset San Jose in six games in the opening round of the playoffs, and their spectacular regular season was quickly forgotten.