1999 was the year that Chris turned 17 years old. This year saw Pokémon become a massive phenomenon in America, with Chris ever so active in the community; he began making Pokémon-themed sites, and even got into the news while playing the Pokémon TCG at his local Books-A-Million. This was also the year Chris began attending the GAMe PLACe. In short, 1999 was the year that the seeds for Chris's life in the 21st century were sowed.
- 10 January - Chris creates an illustrated timeline of the various amendments to the United States Constitution for his high school U.S. Government class.
- 13 January - Chris receives a perfect score on a review sheet for Chapter 10 of his U.S. Government book.
- 19 January - Chris writes 13 Lucky Writing Tips for his English class.
- 31 January - Family Guy debuts on Fox.
- 3 February - Chris completes (and fails) the "Describing Development" assignment for his parenting class.
- 8 February - Chris completes a Spanish assignment about adjectives using drawings of video game characters and cartoon characters. He receives a perfect score. This is the earliest evidence of Chris's interest in Pokémon.
- 9 February - Chris completes a worksheet on child development.
- 11-12 February - Chris writes the rough draft of an opinion paper about students working while in high school.
- 19 February - Chris interviews his parents for his parenting class at Manchester High School.
- 23 February - Chris completes a study guide for Chapter 2 of his Parenting textbook. Also, Chris fails a U.S. Government assignment about "WHAT HAPPENS IF I BREAK THE LAW???"
- 24 February - Chris's 17th birthday. He receives a Pro-200 handheld game console and some used N64 and NES games. He also goes to his Korean Presbyterian Church. To commemorate the occasion, Chris evidently completes a drawing, "Bionic Over Autism". This drawing would later be included in Sonichu #6. This is also the day when Espanolic, one of Chris's more racist creations, was born.
- 5 March - Chris creates a study guide for Chapter 5 of his Parenting textbook.
- 10 March - Chris writes an essay to prepare for the SOL test. He proposes that a swimming pool should be added to the campus of Manchester High School.
- 13 March - Vegaton, the evolution of Espanolic, is born.
- 15 March - Chris forms answers for questions that he is to answer for a mock job interview in his chemistry class.
- 24 March - Chris writes the rough draft of an essay about why John F. Kennedy was the best president evar.
- 25 March - Chris writes the final draft of his JFK essay, and receives a grade of "43/50 + 10 typed."
- 25 March - Chris completes a worksheet on prenatal development, for which he receives a grade of 13/20.
- 10 April - Drummor, a noisy Pokémon, is created by our autistic hero.
- 12 April - Chris writes a paper about having to wear an empathy belly for his Parenting class.
- 15 April - Chris neglects to complete an assignment for his U.S. Government class, despite having written his name and the date on the paper.
- 16 April - Chris makes a Luigi Pokémon card.
- 17 April - Christian creates the "original" Pokémon card for Blue, or Snubbull.
- 18 April - Togepi is made as a Pokémon card by Chris.
- 23 April - Mixed Up Farfetch'd and Missingno. are created as Pokémon Cards by Chris.
- 23 April - Chris melts down as he attempts to complete a quiz on Judicial Branch Terms for his U.S. History class, writing "WHY????!!!!!" on top of his paper. He failed the quiz.
- 23 April - Chris creates his outline for an English essay on the relationship between Japan and the United States during World War II.
- 24 April - Luigi, everyone's favorite Nintendo character, is made into an "original" Pokémon card by Chris, as well as Baniru, or Marrill, and Sonic the Hedgehog.
- 25 April - The domain for CWC's Pokésite 1 in the Pokémon Community is reserved, by someone going by the name Starplayer, for use by Chris.
- 3 May - Chris fails to follow directions when completing an assignment about the constitution for his U.S. Government class.
- 4 May - Chris writes his essay on the relationship between Japan and the United States during World War II.
- 5 May - Chris creates the works cited, or "Trabajos 'Cited'", page for his Japan essay and types it.
- 5 May - Bushwacked, a grass Pokémon, is made into a Pokémon card by Chris.
- 10 May - Chris completes a test for Chapter Five of his U.S. Government textbook and correctly answers each question on one side, but fails to complete the other side of the test, resulting in his failure.
- 6 June - Chris's English teacher gives Chris a report concerning his grades on various assignments and his final grade for the term/year. He received a D+ in the term and a 78 for the year.
- 1 July - In an attempt to promote his own website, Chris posts a comment on the guestbook of a website called Lione Productions.
- 3 July - Bob and Barb sign the guestbook of CWC's Pokésite 1.
- 6 July - Koffingroo, a poisonous kangaroo Pokémon, is born.
- 16 July - A number of new Pokémon are created by Chris on this day, such as Cymbolic, a cymbal Pokémon, Flashbulb and Coonbulb, light bulb Pokémon, and Bugzapp, an insect Pokémon.
- 22 July - Christian launches CWC's Pokésite 2.
- 29 July - A friend signs Chris's guestbook and tells him that she hopes he continues learning HTML.
- August/September - Christian begins his senior year at Manchester High School.
- 15 August - Chris makes a Duelist magazine cover featuring his custom Pokémon cards.
- 17 August - Weeler and Hotfinish, vehicle Pokémon, are born.
- 18 August - Strongtire, a robot Pokémon, is born.
- 24 August - Compufrog, a Pokémon "made from computer programming," is born. Also, Chris edits his Snubbull card to its correct name.
- 25 August - Chris creates his Pokédex trainer card.
- 27 August - Chris updates his Marrill card to its correct name.
- 30 August - Chris makes Yoshi, ANOTHER copyrighted character, as a Pokémon.
- 4 September - Bob turns 72.
- 9 September - The North American release of Sega's last console, the Dreamcast.
- 10 September - Birth of Lillie Celeste Simpsons
- 22 September - Chris writes his own myth - "How the Pokémon Came into Our PokéBalls". According to Chris, his English teacher thought it was great.
- 26 September - Chris creates the Christian W. Chandler trainer card.
- 30 September - A friend, Mrs. Johnson, signs Chris's guestbook and says that she knows of "others" that would like his website and she will pass it on to them.
- 1 October - Barb turns 58.
- 7 October - Excel Saga anime premieres.
- 13 October - Chris launches the news section on his new Pokémon site and posts the first two articles.
- 14 October - Chris posts on his site regarding a Pokémon contest for a trip to Australia.
- 16 October - Chris is featured in PokéNews, dressed up as Ash.
- 20 October - Chris reports on his site about new Pokémon cards.
- 22 October - Chris posts information on his site about three Pokémon.
- 28 October - Chris posts on his site about another Pokémon contest.
- 30 October - Chris publishes "How the Pokémon Came into Our PokéBalls" on his Pokémon site.
- 4 November - Chris updates an article on his Pokémon site about a Burger King tie-in.
- 16 November - Chris starts a list of promo cards on his website.
- 18 November - Chris apologizes for not updating his website recently because he had homework.
- 21 November - Pokémon Gold and Silver are released in Japan. First appearance of Sneasel.
- 22 November - Chris makes Plautistic, one of his only useless Pokémon.
- 25 November - Chris makes Donphan, an already existing Pokémon, into one of his "originals."
- 30 November - Chris reprints a Pokémon timeline from a local newspaper on his website.
- 5 December - A Pokémon fan signs his website guestbook.
- 9 December - Chris signs the guestbook of Lione Productions once more.
- 15 December - Chris reports on a new Pokédex on his Pokémon site.