| Year | Tobi | SRB2 | SRB20YA |
| 1730 (1750) | Tobi's great-great-great-great-great-grandfather (Samuel) is born. | ||
| 1767 (1787) | Tobi's great-great-great-great-grandfather (John Sr.) is born. | ||
| 1770 (1790) | Tobi's great-great-great-great-great-grandfather (Samuel) dies. | ||
| 1808 (1828) | December 2nd - Tobi's great-great-great-grandfather (John Jr.) is born. | ||
| 1849 (1869) | January - Tobi's great-great-great-great-grandfather (John Sr.) dies. | ||
| 1850 (1870) | March 10th - Tobi's great-great-grandfather (George) is born. | ||
| 1877 (1897) | February 11th - Tobi's great-grandfather (Thomas) is born. | ||
| 1888 (1908) | January - Tobi's great-great-great-grandfather (John Jr.) dies. | ||
| 1912 (1932) | March 11th - Tobi's grandfather (Dennis) is born. | ||
| 1934 (1954) | March - Tobi's great-great-grandfather (George) dies. | ||
| 1936 (1956) | September 30th - Tobi's father (Christopher) is born. | ||
| 1947 (1967) | June - Tobi's mother is born. | ||
| 1951 (1971) | November - Tobi's great-grandfather (Thomas) dies. | ||
| 1967 (1987) | March 11th - Tobi's grandfather (Dennis) dies. | ||
| 1983 (2003) | November 21st - Tobi is born. | ||
| 1984 (2004) | November 21st - Tobi turns 1. | ||
| 1985 (2005) | November 21st - Tobi turns 2. | ||
| 1986 (2006) | Sometime before turning 3 - Tobi is diagnosed with autism. November 21st - Tobi turns 3. |
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| 1987 (2007) | September - Tobi begins at his first school. November 21st - Tobi turns 4. |
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| 1988 (2008) | November 21st - Tobi turns 5. | ||
| 1989 (2009) | August 12th - Tobi undergoes a heart operation to patch three holes in the heart. November 21st - Tobi turns 6. |
November 27th - SSNTails releases source code archives for Halloween 1.32, Christmas 0.96, and "Demo 4.2" | |
| 1990 (2010) | November 21st - Tobi turns 7. | July 7th - SSNTails releases an archive containing level WADs ranging from 1998-2001. | |
| 1991 (2011) | November 21st - Tobi turns 8. | ||
| 1992 (2012) | June/July - Earliest evidence of Tobi playing SRB2. November 21st - Tobi turns 9. |
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| 1993 (2013) | November 21st - Tobi turns 10. | ||
| 1994 (2014) | February - Tobi leaves his first school. November 21st - Tobi turns 11. |
June 10th - SSNTails releases an archive of early art assets. November 16th - SSNTails releases old storyboards. |
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| 1995 (2015) | March - Tobi begins at his second school. July - Tobi finishes primary school. September - Tobi begins education at his third school. October/November - Tobi leaves his third school. November 21st - Tobi turns 12. |
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| 1996 (2016) | November 21st - Tobi turns 13. | October 4th - Jeff Read releases his Sonic Doom mod. | |
| 1997 (2017) | January 20th - Tobi begins education at his fourth school. September - Tobi begins learning basic HTML in IT class. November 21st - Tobi turns 14. |
March - SSNTails discovers Jeff Read's Sonic Doom, and decides to make his own. May - Sonikku begins development of SRB1. July 4th - SRB1 v1.0b released. September 7th - SRB1 v1.1a released. October - Sonic Doom 2 development begins. December 12th - Last modified date of SSNTails' Sonic Doom. |
May - SRB20YA begins, initially called "The SRB2 of 2 Decades Ago". It was a spontaneous magazine in TXT format. |
| 1998 (2018) | May 19th - Tobi leaves his fourth school. September - Tobi loses sight in one eye due to optic nerve malfunction. November 21st - Tobi turns 15. |
February 1st, 6:17pm British time - SRB1 is completed. February 11th - SRB1 v1.3f released. March 8th - Development of SRB2 begins. April - Build of downloadable TGF build. May - Sonic Team Junior formed. July - TGF abandoned for a new C engine written by Stealth. August - Stealth goes AWOL, SSNTails begins work on a 3D version of SRB2 on the Doom Legacy engine. December - Sonic Doom 2 v4.0 released. December 24th - SRB1 Christmas is released. |
February 27th - Dev Pack 1 is released by Glaber with permission from SSNTails. March - Format changes from a TXT format to a HTML format. March 11th - Dev Pack 2 is released by Glaber with permission from SSNTails. |
| 1999 (2019) | November 21st - Tobi turns 16. | March - Build of SRB2 as a WAD with two levels and incomplete Crawla sprites. September 5th - White Gloves Diaries begins. August - Source code modifications begin. September 14th - A backup of the source code is sent to Saxman. October 31st - Halloween v1.0 released. December 10th - Official website moves to SSRG. December 24th - Christmas v0.90 is released and recalled shortly after. |
August - During an event on Omniarchive (Minecraft archival server), Tobi meets SteleCat, the person behind "Minecraft 10 Years Ago". Tobi would join the crew sometime after. Autumn - Tobi begins conceptulizing a website, only on one HTML file at the time. October 31st - "The SRB2 of 2 Decades Ago" is changed to "Sonic Robo Blast 2 Decades Ago" (SRB2DA). December - Tobi launches the official SRB20YA website, initially on 000webhost. |
| 2000 (2020) | November 21st - Tobi turns 17. | February 22nd - Christmas v0.92 released. March 5th - A large amount of assets (including WADs and binaries, along with source code) are sent to Saxman. March 24th - Christmas v0.93 released. April 24th - Christmas v0.94 released. September 9th - SRB2 makes an appearance at SAGE 1 with a preview video. September 9th - Christmas v0.96 is released on CD as a prize and to order for $5 ($10 outside US). October - Halloween v1.32 released. November 13th - Demo 1 released. December 25th - Demo 2 preview video released. |
February 24th - "SRB2DA" changed to "SRB20YA". March 23rd - Discord server created. April 7th, 8:13pm GMT - Discord server reaches 100 messages. May 8th - Tobi moves the site to a friend's server. May 15th - Tobi moves the site again, to NeoCities. May 20th - The site reaches 100 visits. July 4th - The site reaches 1,000 visits. December 11th - SSNTails joins the Discord server. December 14th, 6:00pm GMT - Discord server reaches 1,000 messages. |
| 2001 (2021) | November 21st - Tobi turns 18. | March 5th - Demo 2 released. March 9th - SRB2 website opens. SRB2 also appears at SAGE 2. June 23rd - Demo 3 released. July 18th - Demo 3 Era Prototype built. December 12th - Christmas 0.96 Windows update released. December 25th - Demo 4 released. |
February 21st - SSNTails releases early 2.0 Egg Rock Zone WADs from ~March 2009. February 26th - Sonikku joins the Discord server. March 1st - The site reaches 10,000 visits. June 29th, 9:50pm BST - Discord server reaches 10,000 messages. November 15th - YouTube channel reaches 100 subscribers. |
| 2002 (2022) | February 3rd - Tobi has a back operation to correct lumbar scoliosis. November 21st - Tobi turns 19. |
January 6th - Demo 4.1 released. March 8th - Demo 4.32 released. SRB2 also appears at SAGE 4. March 12th - Demo 4.33 released. March 15th - Sonic Stadium interview. March 16th - Demo 4.34 released. March 20th - Demo 4.35 released. |
April 8th - SSNTails releases the July 18th, 2001 as well as the August 22nd and September 22nd, 2008 builds. December 18th - In partnership with Glaber Co., SRB2 The Past 2.0 is released. |
| 2003 (2023) | March 15th - An accidental hard drive wipe occurs. June 14th-18th - Tobi's Discord account is compromised. November 21st - Tobi turns 20. |
March 9th - Tournament 2003 released. June 19th - Final Demo 1.01 released. June 19th - Final Demo 1.02 released. June 19th - Final Demo 1.03 released. June 19th - Final Demo 1.04 released. |
March 9th - GitHub site beta testing begins. July 1st - NeoCities website closes down. July 4th - Discord server reaches 100,000 messages. August 17th - SSNTails locates a developer snapshot of 1.1 from September 2008, containing WAD files and the September 24th build. August 19th - Saxman sends SSNTails a ZIP of SRB2 files, including contemporary binaries, assets, and source code from March 5th, 2000. October 15th - Website moves to srb20ya.org. |
| 2004 (2024) | November 21st - Tobi will turn 21. | January 1st - Final Demo 1.08 released. | March 2nd - SSNTails releases the September 14th, 1999 source code backup to GitHub. March 9th - SSNTails releases the March 5th, 2000 assets to GitHub. |