Ah now I can see the reasoning with Order of Shadows - interestingly enough, there is a 'statue' of Haunted Castle Simon in Medusa's lair in OoS, if that gives you any more fodder for your theories.
Potentially it does and the reasons are below, depending on what the statue means, and why it's there in the first place.
I heard Iga didn't want OOS inserted into the timeline, where as the the other creator did because he thought Iga was too strict with his "timeline guidelines".
For the following scenarios I am still assuming OOS takes place outside of the main timeline as per the established canon.
Scenario (A)- The Statue is there to remove OOS from the main timeline (referencing HC Simon)
- HC's Simon was the son of Sonia, the Legends ending states that her child will rise to face Dracula.
- He defeated Dracula once prior to Desmond, and for some reason a statue of him was erected/ manifested in Medusa's lair when Castlevania appeared.
- This placement allows VK/ XX to fit at the end of the timeline as its prologue states "Hundreds of years after Simon Belmont defeated Dracula." (basically switching HC with SCIV)
<<<<<<<<<<<<<<[Judgement]>>>>>>>>>>>>>>>
Legends>HC>OOS>LOD>64>VK
/
LOI>CVIII>COD>TA/AR>BR>CVC>CVII>HOD>ROB>SOTN>OOE>BL>POR>>>AOS>DOS
\
\
SCIV>>>>>/>>>>COTM
Scenario (Bi) - The Mindf*** Loop- The Statue places OOS in the existing HC timeline
- Simon from HC went to face Dracula but lost when he was turned to stone by Medusa's gaze, along with the VK.
-
If HC Simon wins instead of losing to Medusa, SCIV happens after HC and the same Simon defeats Dracula again i.e.
HC>SCIV>LOD>64>VK- The "Hunter Whip" was then born as with a new clan descended from the Belmonts (partly by blood, but not by name)
- Desmond faces and defeats Dracula with the "Hunter Whip", not the VK.
- Dracula perishes but Castlevania does not fall.
<<<<<<<<<<<<<<[Judgement]>>>>>>>>>>>>>>>
Legends>
SCIV>LOD>64>VK /
lLOI>CVIII>COD>TA/AR>BR>CVC>CVII>HOD>ROB>SOTN>OOE>BL>POR>>>AOS>DOS
\
l \
l HC>OOS>COTM
Scenario (Bii)- The Statue places OOS in the existing HC timeline
- Simon from HC went to face Dracula and won.
- COTM is not necessarily connected to HC>OOS
- Dracula perishes but Castlevania does not fall (because there was supposed to be a sequel.)
<<<<<<<<<<<<<<[Judgement]>>>>>>>>>>>>>>>
Legends>SCIV>LOD>64>VK
/
LOI>CVIII>COD>TA/AR>BR>CVC>CVII>HOD>ROB>SOTN>OOE>BL>POR>>>AOS>DOS
\
\
HC>OOS>/>COTM
Scenario (Bii) - version 2- Same as Bii except HC>OOS>LOD>64 is its own timeline
- Legends>SCIV>VK is its own timeline
- COTM is its own timeline
<<<<<<<<<<<<<<[Judgement]>>>>>>>>>>>>>>>
COTM
/
Legends>SCIV>VK
/
LOI>CVIII>COD>TA/AR>BR>CVC>CVII>HOD>ROB>SOTN>OOE>BL>POR>>>AOS>DOS
\
\
HC>OOS>LOD>64
Scenario (C)- Merging of elements from A and B
- HC Simon is Sonia's son, defeats Dracula, a statue commemorating this manifests in Medusa's lair because: irony.
- Desmond only defeats The Guardian of Dracula's sleeping spirit c.1666, who remains dead until either c.1691 or 1752 (100 years prior to CV 64 when
- In 1691/ 1752, Dracula's spirit actually awakens from it's slumber (with no Guardian protecting it)
- SCIV Simon (another Simon or Simon II) faces the real Dracula and defeats him.
<<<<<<<<<<<<<<[Judgement]>>>>>>>>>>>>>>>
COTM
/
Legends>HC>OOS>>>SCIV>LOD>64>VK
/
LOI>CVIII>COD>TA/AR>BR>CVC>CVII>HOD>ROB>SOTN>OOE>BL>POR>>>AOS>DOS
Scenario D- Merge elements of A-C and assume Desmond Richter from VK/ XX is using the "Hunter Whip"
<<<<<<<<<<<<<<[Judgement]>>>>>>>>>>>>>>>
Legends>HC>OOS>>>SCIV>COTM>LOD>64>VK
/
LOI>CVIII>COD>TA/AR>BR>CVC>CVII>HOD>ROB>SOTN>OOE>BL>POR>>>AOS>DOS
Scenario ENothing happens because the statue doesn't mean anything (except OOS not being canon) and my timeline remains because I'm a boss:
<<<<<<<<<<<<<<[Judgement]>>>>>>>>>>>>>>>
Legends>SCIV>OOS>LOD>64>VK
/
LOI>CVIII>COD>TA/AR>BR>CVC>CVII>HOD>ROB>SOTN>OOE>BL>POR>>>AOS>DOS
\
\
HC>>>>>/>>>>COTM