January 2008

- Ted starts his ten sessions with Dr. Stella Zinman, to get his tattoo removed [313 Ten Sessions. The last session was in March, so January is ten weeks before this]

February 2008

- Lily arrives back from Aspen with a 6pack of Aspen Yards Ale for Marshall [413 Three Days of Snow]​

March 2008

- A guy named Mitch tries out a new move called The Naked Man on two girls in subsequent dates and it works both times. [According to Mitch in 916 How Your Mother Met Me he says he's tried it and it worked twice, starting a few weeks before St Patricks Day 2008 when he tries a third time on Tracy]

- 17th. Ted & Barney go to a bar called Low Point on St Patricks day and after behaving like a jackass Ted gets punched in the face. [312 No Tomorrow]​.

Tracy and her friend Kelly also go to the same bar where Tracy runs into Mitch (aka The Naked Man), her instructor from orchestra camp. She invites him back to her apartment to give him her cello and leaves her yellow umbrella at the club. Back at Tracy's apartment Mitch tries to use his Naked Man move on her but she declines (giving him his success rate of "Two out of three times"). Mitch encourages Tracy to follow her dreams, which she says is to end poverty. She later realises that she left her umbrella at the club, but it's closed by the time she realises. [916 How Your Mother Met Me]

- 18th. The day after the party Barney wakes up in a dumpster near his apartment. Ted returns to the club Ted goes back to get his cellphone,and ends up leaving with Tracy's umbrella. She's upset to find it's gone by the time she returns to the club [312 No Tomorrow, 916 How Your Mother Met Me.]​

 After ten sessions with Stella she finally agrees to go on a date with Ted [313 Ten Sessions]
- Late March. Marshall and Ted bet on college basketball, Barney tries to find out who the mystery woman is who has been sabotaging his hookups [314 The Bracket]​

April 2008

 - Marshall quits his job at Nicholson, Hewitt & West [315 The Chain Of Screaming]. ​He later goes to beg for his job back but has because of Lily's kindergartners he has lice, 2 weeks later his boss is arrested. [320 Miracles]​

- Robins ex-boyfriend Simon visits from Canada and they date again briefly, Robin shows Barney her Robin Sparkles video "Sandcastles in the Sand" and afterwards they make out [316 Sandcastles in the Sand]​

- 25th. Teds 30th Birthday, Barney tells him about his hook-up with Robin and Ted tells him they are no longer friends. [317 The Goat]​

- Sometime in April. Ted's sister Heather is busted for shoplifting. [In 411 Little Minesota Ted says this happened eight months ago]

May 2008

 - Ted and Stella have sex for the first time [318 Rebound Bro]​

- Lily and Marshall are forced to sell things to raise money to pay to fix the slanted floor in their apartment, Lily sells her paintings to a vet, Barney discovers Stella's receptionist Abby is the one who has been sabotaging his hookups [319 Everything Must Go]​

- Marshall jinxes Barney but he doesn't take it seriously. Later that day he's hit by a bus and is badly hurt. From that point forward he takes jinxes very seriously.  [The jinx is mentioned in 811 The Final Page Part One. He's in the accident "Six months before Nov" according to 320 Miracles]​.

- Ted is in a car accident which makes him re-examine his life. He proposes to Stella and she accepts. ["Six months before Nov" 320 Miracles]​

June-September 2008

- B​arney goes through physical therapy, Marshall copes poorly with unemployment [401 Do I Know You]​

September 2008

 - Lily finds out about Barney's crush on Robin. 2 days later she tells Marshall [401 Do I Know You, 424 The Leap]

- Stella watches Star Wars for the first time [401 Do I Know You]​

- 29th. Marshall gets a job at Goliath National Bank, For the first time since 2000 Marshall eats the best burger in New York [Date mentioned in 402 Best Burger In New York]​

October 2008

- The gang visits Stella's home in New Jersey. [403 I Heart NJ]​

- Robin quits her job at Metro News 1 and decides to take a job in Japan.  [403 I Heart NJ]​ 

- Lily and Marshall move into their new apartment. [404 Intervention]

- Stella's sister Nora's wedding is cancelled and so Stella and Ted take the date for their own wedding. [405 Shelter Island]

- Robin is depressed about Ted and Stella's upcoming wedding and gets really drunk. She takes Lily to Central Park, and digs up the locket she left there in 1994 to use as her something old. She tells Lily she intends to take it to Japan but she's so drunk Lily thinks she won't remember it so she puts it in a racecar pencil box for her to safely take it with her. Robin doesn't remember any of this and somehow Ted ends up with the racecar pencil box, though he has no idea there's a locket inside it. [824 Something New. Exactly dating this is difficult - it's after Robin gets a job in Japan but before she moves there. This is the most likely placing of the event]

- 31st. Lily and Marshall fight over their halloween costumes as Marshall wants them to go as penguins but Lily says penguins are stupid. [2 years ago from 2010 according to 518 Say Cheese]

November 2008

- Robin moves to Japan to be a newsreader for the top rated English news channel. [405 Shelter Island]

- On their wedding day Stella leaves Ted for her ex-boyfriend Tony [405 Shelter Island, Date established as being 6 months after 320 Miracles]​. 

- Ted wakes up the following morning after getting left at the altar with a really bad hangover and Barney gives him his Stinson Hangover Fixir Elixir. [The day after he got left at the altar according to 918 Rally].

- One week after Ted is left at the altar attends his high school friends, Joel and Mora's wedding and cries during the toast. [In 701 The Best Man Ted states he was left at the altar "a week ago"]

- Two weeks after he's left at the altar Ted sees Stella in a restaurant [406 Happily Ever After]​

- Ted gets the job of working on the Goliath National Bank new building project, beating Swedish architecture firm, Sven [408 Woooo!]​

- Robin dates Mitch, who teaches the gang his 'Naked Man' move. [409 The Naked Man]​

December 2008

- Ted and Barney are sued for assault after they get involved in a fight [410 The Fight]​

- Teds sister Heather moves to New York [411 Little Minnesota]​

- 31st. Marshall and Lily fall asleep on the couch waiting for New Years [413 Three Days of Snow]​

Unknown 2008

- Barney's Birthday. The gang celebrates at MacClarens and Ted as usual brings a random girl he thinks is the one but doesn't remember the name of a year later. When Slash from Guns N Roses comes in the bar and they get a photo with him the gang is annoyed that when they see the photo to find that the random girl is blocking Slash. [518 Say Cheese]​