January 2006

- Claudia & Stuarts wedding, Ted meets Victoria and the two later begin dating. [112 The Wedding]​

- Robin anchors Metro News 1 for the first time. [112 The Wedding]​
March 2006

- Victoria leaves for a fellowship in Germany and Ted and her decide to try dating long distance. [116 Cupcake]​

- Lily destroys an expensive wedding dress. [116 Cupcake]​

- Marshall starts an internship at Barney's office. [117 Life Among The Gorillas]

- While throwing pencils one bounces up into Barneys nose. [320 Miracles]​
April 2006​

- Ted & Victoria break-up, [118 Nothing Good Happens After 2AM]

- Victoria starts dating Klaus, who's in her culinary class in Germany. [According to 703 Ducky Tie they started dating a day and a half after she broke up with Ted]

- Robin wins a Local Area Media Award (LAMA) for a story she did as a reporter on Metro News One. [119 Mary The Paralegal]​

- Marshall decides to run the marathon. [215 Lucky Penny]
- 25th. Ted's 28th birthday. [121 Milk]​

- 26th. Ted gets a call from Love Solutions saying they've found him a match. [121 Milk]​

May 2006

- Ted begins dating Robin, Lily goes to San Francisco for an art fellowship and breaks up with Marshall. [122 Come On]​

Between May and September 2006

- 34 days after Lily leaves Marshall. He calls her only to find she's changed her number. [34 days after 122 Come On, 201 Where Were We?]​

- 41 days after Lily leaves Barney takes Marshall to a strip club. [41 days after 122 Come On, 201 Where Were We?]​

- 44 days after Lily leaves Ted takes him to a New York Yankee game  [44 days after 122 Come On, 201 Where Were We?]​

- 46 days after Lily leaves Marshall Robin takes him to a gun range in an attempt to help him get over Lily [46 days after 122 Come On, 201 Where Were We?]​
 - Marshall finds Lily's credit card bill. The day after he finds out she is back in New York but it turns out her credit card had been stolen. [Likely occured in August. 55 days after 122 Come On, 201 Where Were We?]​

- Unknown Date. Trilogy time 2006. As per tradition Marshall, Ted and Barney watch the Star Wars trilogy and imagine what their lives will be like in 2009. Ted is sure that Lily will be back by then and will be married to Marshall, while Marshall is more certain she'll be married to a moustached man with a trucker hat. [720 Trilogy Time. It is uncertain exactly when the Trilogy Time occured but it is sometime between May and September.]

- Sick of Marshall being depressed Barney flies to San Francisco and sees Lily and gives her a ticket home, saying that she's made a mistake and Marshall misses her. He also tells her that if she reveals he's done this he'll deny it [revealed in 219 Bachelor Party].
September 2006

- For the first time since Lily left Marshall makes pancakes on a Sunday. [67 days after 122 Come On, 201 Where Were We?]​

- Lily returns to New York and begins looking for a new apartment. [201 Where Were We?]​

- Still reeling from her break-up with Marshall Lily listens to her break-up song, "Fly" by Sugar Ray. She decides to get a tattoo of Sugar Ray but Gary Blauman stops her when it's only partially done and convinces her it's a mistake because he knows that her and Marshall will get back together. [921 Gary Blauman]

- Ted finds a 1939 penny while riding the subway. He manages to get $1.50 for it from a collector and buys Robin and him hot dogs. While walking the two spot a store advertising wedding dresses. This starts a chain of events that eventually results in Ted missing a flight to Chicago in a few months time [*1 See Notes below. 202 The Scorpion and The Toad, 215 Lucky Penny]

October 2006

- Ted's parents visit New York and Robin meets them for the first time. Ted finds out his parents have divorced [203 Brunch],

- Barney and Teds mother kiss after he drops her off at the airport. [520 Home Wreckers]​

- Ted & Robin have their first fight. [204 Ted Mosby: Architect]

- Lily works at an Hawaiian restaurant and at Ted's architecture firm before returning to teaching kindergarten [206 Aldrin Justice]​

- 30th. Barney dresses up as Borat for Halloween…a day early [30th Oct, a year before 309 Slapsgiving]​

November 2006

- 5th. After Marshall breaks his toe and is unable to run the marathon he's been training for Barney runs the marathon for him. Afterwards Barney is so tired he gets stuck on the subway and calls Ted to rescue him. Ted jumps a turnstile to try and save him and is arrested.  [215 Lucky Penny. In reality the New York City Marathon happened on this day.]​

- Marshall and Lily get back together. [207 Swarley, "six months after Lily left him"]​

- Marshall and Lily decide to elope in Atlantic City. They change their mind but are accidentally married for 12 seconds. [208 Atlantic City]​

- The gang find out about Robin's past as Robin Sparkles and watch Let's Go To The Mall. Barney loses to Marshall in a slap bet over whether Robin's video was of her in a porno and Marshall gets the right to slap Barney five times. [209 Slap Bet]​

- Barney's brother James comes for a visit and Barney finds out he's dating a guy named Tom. [210 Single Stamina]

- 23rd. Thanksgiving. Ted and Robin have sex seven times. [Ted mentions this happened a year ago in 309 Slapsgiving]
December 2006​

- 15th. Two armed robbers try to rob The Apartment but are stopped by a gun-wielding Robin. [409 The Naked Man]

- 24th. Lily & Ted fight after Lily finds a phone message Ted left while she was in San Francisco calling her a grinch. [211 How Lily Stole Christmas]​

- Christmas. Ted brings a random girl (Leilani) to the gangs Christmas who he claims is the one. Four years later he can't even remember her name [Four years ago according to 518 Say Cheese]​
 - Sometime in December Lily & Marshall form a friendship with their new neighbours, Michael & Laura Gerard, which goes later bad [Mentioned as happening in December 2006 in 311 The Platinum Rule]​

Sometime in 2006

- Lily brings her co-worker, Shelly, to MacClarens to meet Ted but he's stuffing his face with chicken fingers so she pretends he's not there and they leave. [3 years before 508 The Playbook]

- Lily goes to visit her grandparents and finds her dad living with them and the financial strain he's causing means her grandparents can't retire, and her grandfather has to go back to work. She's so furious she doesn't see her father for three years following this. [509 Slapsgiving 2: Revenge Of The Slap]

- Marshalls all lawyer band The Funk, The Whole Funk and Nothing But the Funk plays their only gig. [According to 603 Unfinished it was four years ago]​

- Marshall drops a calzone and then picks it up and then eats it, which is witnessed by Barney. [618 A Change of Heart]​

- Marshall, Lily & Ted dress up as Dr Frankenstein & his monster and a scared villager [704 Stinson Missile Crisis]​

 

Notes:

*1 - Dating is based on the fact that in The Scorpion And The Toad that Ted mentions he found a 1939 penny. Ted and Robin getting hot dogs etc is from Lucky Penny. The clothing they wear in the flashback in Lucky Penny is the same as in The Scorpion and The Toad, meaning it occured on the same day as those events. This creates and inconsistency though as at this time Lily and Marshall were broken up, and wouldn't get back together for another two months so there's no way Lily was even thinking about buying a wedding dress.