NHL 2K10

Use your right analog stick [RS] to bring up the 2K menu after the loading screen and select "Game Modes" at the bottom.

Select "Season"..."New"....

In the next screen which pops up, make sure the following is set (if I don't list it below, it does not matter what you select):

Season Settings = NHL
AutoSave = Off (so you can reload and try again for the "Red Wings Trophy" achievement)
Season Length = any # you want; I used the minimum of 29
Trade Deadline = Off (simulation goes faster)
Trade Override = Off
Allow CPU Trades = Off
Injuries = Off
Fantasy Draft = None
Customize League = Off
Period Length = 1 minute

Once everything is set, press "Start" to advance...

In the next screen, SELECT ALL 30 TEAMS, then press "Start" to Advance. In the next screen, "NHL Task Automation", I don't think it matters what any of these are, but I set "Lineup Management" and "Simulation Strategy" to "On". Press "Start" to advance again...

At the next screen, "NHL.com", press "Start" on your controller, scroll down and select "Simulate Season". Simulating is real fast, and should take less than a few minutes...

After the regular season is done simulating, you will get a notice that the Playoffs have started. At this point, the achievement for "Capitals Trophy" will pop up!

Continue to simulate through the end of the Stanley Cup Playoffs and if you are lucky, the Red Wings Trophy achievement will also pop.

This solution also works for:

and (maybe):

now you can play though the whole season and get this achievement and you will most likely get it unless you are really bad at playing this game if thats the case you can always just pick a strong team like the red wings and sim the season