The 2008–09 NHL season saw a dramatic Finals rematch. This time, the Pittsburgh Penguins defeated the Detroit Red Wings in seven games, with Sidney Crosby becoming the youngest captain to win a Stanley Cup. Evgeni Malkin won the Art Ross and Conn Smythe trophies, solidifying the Penguins as a powerhouse. The season was also notable for the "Green Monster" line in Boston and the rise of the Chicago Blackhawks’ young core. Alexander Ovechkin continued his goal-scoring dominance, securing his second consecutive Hart Trophy as the league's MVP.
| vs previous season | ||||||
| Rank | Player | NHL Salary ($US) | In today's $ | +/- ($) | +/- (%) | |
| 1 | Dany Heatley | $10,000,000 | $14,969,810 | $4,500,000 | 82% | |
| 2 | Sidney Crosby | $9,000,000 | $13,472,829 | $5,300,000 | 143% | |
| 2 | Alex Ovechkin | $9,000,000 | $13,472,829 | $8,015,800 | 814% | |
| 4 | Miikka Kiprusoff | $8,500,000 | $12,724,338 | $4,900,000 | 136% | |
| 5 | Glen Sather | $8,000,000 | $11,975,848 | $5,000,000 | 167% | |
| 5 | Jason Spezza | $8,000,000 | $11,975,848 | $3,000,000 | 60% | |
| 5 | Wade Redden | $8,000,000 | $11,975,848 | $1,500,000 | 23% | |
| 5 | Daniel Briere | $8,000,000 | $11,975,848 | -$2,000,000 | -20% | |
| 5 | Thomas Vanek | $8,000,000 | $11,975,848 | -$2,000,000 | -20% | |
| 5 | Scott Gomez | $8,000,000 | $11,975,848 | -$2,000,000 | -20% | |
| 5 | Kimmo Timonen | $8,000,000 | $11,975,848 | |||
| 12 | Brad Richards | $7,800,000 | $11,676,451 | |||
| 13 | Henrik Lundqvist | $7,750,000 | $11,601,602 | $3,500,000 | 82% | |
| 14 | Ilya Kovalchuk | $7,500,000 | $11,227,357 | $2,000,000 | 36% | |
| 14 | Zdeno Chara | $7,500,000 | $11,227,357 | |||
| 14 | Marian Gaborik | $7,500,000 | $11,227,357 | $1,000,000 | 15% | |
| 17 | Nicklas Lidstrom | $7,450,000 | $11,152,508 | -$150,000 | -2% | |
| 17 | Marian Hossa | $7,450,000 | $11,152,508 | $450,000 | 6% | |
| 19 | Ryan Smyth | $7,250,000 | $10,853,112 | -$250,000 | -3% | |
| 20 | Gary Bettman | $7,230,000 | $10,823,172 | $130,000 | 2% | |
| 21 | Joe Thornton | $7,200,000 | $10,778,263 | $530,000 | 8% | |
| 22 | Vincent Lecavalier | $7,166,666 | $10,728,363 | -$1 | 0% | |
| 23 | Brian Campbell | $7,142,857 | $10,692,721 | $5,392,857 | 308% | |
| 24 | Chris Drury | $7,100,000 | $10,628,565 | |||
| 25 | Jaromir Jagr | $7,000,000 | $10,478,867 | -$1,360,000 | -16% | |
| 25 | Jarome Iginla | $7,000,000 | $10,478,867 | |||
| 25 | Roberto Luongo | $7,000,000 | $10,478,867 | $500,000 | 8% | |
| 25 | Dion Phaneuf | $7,000,000 | $10,478,867 | $6,057,600 | 643% | |
| 25 | Lubomir Visnovsky | $7,000,000 | $10,478,867 | $4,948,000 | 241% | |
| 25 | Michal Rozsival | $7,000,000 | $10,478,867 | $4,700,000 | 204% | |