| card/ date | match | match type | title(s) |
|---|
 IWA-MS The Eyes of March
Mar 12th 2020 | Ronnie Roberts | def. | Drew Dillinger | | |
IWA-MS In Like A Lion 2020
Mar 7th 2020 | Drew Dillinger | def. | August Matthews | | |
IWA-MS Cold War
Feb 27th 2020 | Drew Dillinger | def. | Big Cuz | "I Quit" | |
IWA-MS FebuBRAZY
Feb 13th 2020 | Big Cuz | def. | Drew Dillinger | "I Quit" | |
IWA-MS This Means War
Jan 30th 2020 | Drew Dillinger | def. | Big Cuz | "Last Man Standing" | |
IWA-MS All Or Nothing
Jan 16th 2020 | Big Cuz | def. | Drew Dillinger | Old School Rules | |
IWA-MS Out With The Old, In With The New 2020 - Day 2
Jan 4th 2020 | Drew Dillinger | def. | Lincoln Mosely | | |
IWA-MS Out With The Old, In With The New 2020 - Day 1
Jan 2nd 2020 | Drew Dillinger | def. | Big Cuz | | |
IWA-MS Christmas Stampede
Dec 26th 2019 | Michael Hayes | def. | Aaron Williams, Big Cuz, Brandon Taggart, C. J. Hatler, Drew Dillinger, Joe Travis, Joshua Rupiper, Kayla Kassidy, Lincoln Mosely, Loki Havik, Lola Perez, Mike Roach, Mr. Wrestling #69, Ray Waddell, Reilly MaGuire, Ronnie Roberts, Stonewall, ThunderKitty, Victor Vargus | Christmas Carnage Come As You Are, Bring What You Want Match | |
IWA-MS Christmas Stampede
Dec 26th 2019 | Lola Perez & Ronnie Roberts | def. | Big Cuz & Drew Dillinger | falls count anywhere (tag) | |
IWA-MS Seasons Beatings 2019
Dec 12th 2019 | Larry D | def. | Drew Dillinger | | |
IWA-MS Big Ass Christmas Bash 2019
Dec 7th 2019 | Drew Dillinger | def. | PB Smooth | | |
IWA-MS Wrestlefeast 2019
Nov 28th 2019 | Alice Crowley & Drew Dillinger & Loki Havik & The Zodiak | def. | Kayla Kassidy & Lincoln Mosely & Raul LaMotta & Ronnie Roberts | 8-person tag elimination | |
IWA-MS Man Up
Nov 21st 2019 | Big Cuz & Drew Dillinger | def. | Raul LaMotta & Ronnie Roberts | IWA Rules (tag) | |
IWA-MS She's Still Amazing
Nov 17th 2019 | Joe Travis | def. | A. J. Daniels, Chad Stallings, Drew Dillinger, Joshua Rupiper, Miles Morales, Tom Coffey | 7-way | |
IWA-MS Double Jeopardy
Nov 14th 2019 | Raul LaMotta & Ronnie Roberts | def. | Big Cuz & Drew Dillinger | IWA Rules (tag) | |
IWA-MS I Want It All
Nov 7th 2019 | Ronnie Roberts | def. | Drew Dillinger | | |
IWA-MS The Show Must Go On
Nov 2nd 2019 | Raul LaMotta | def. | Drew Dillinger | | |
IWA-MS The Dirty
May 30th 2019 | Max the Impaler | def. | Corey Roberts, Drew Dillinger, Raul LaMotta, Wayne Moxxi | 5-way | |
IWA-MS Mayhem In May
May 16th 2019 | Brayden Lee | def. | Drew Dillinger | | |
IWA-MS Somebody's Gonna Hurt Somebody 2019
May 9th 2019 | Drew Dillinger | def. | Raul LaMotta | | |
IWA-MS Derby Madness 2019
May 2nd 2019 | Project Monix | def. | Drew Dillinger | | |
IWA-MS We Are IWA 2019
Apr 18th 2019 | Kongo Kong | def. | Drew Dillinger | | |
IWA-MS Thunder Before Thunder
Apr 11th 2019 | Dewey Wellington & Joe Travis & Joshie Boy & Sean Patrick O'Brian | def. | Ben Shearin & Drew Dillinger & Raul LaMotta & The Pizza Guy | 8-person tag | |
IWA-MS Opportunity Hurts
Apr 2nd 2019 | Larry D (c) | def. | Drew Dillinger | | IWA:MS Heavyweight Title
|
IWA-MS Legendary
Mar 28th 2019 | Drew Dillinger | def. | Dewey Wellington | | |
IWA-MS 900th Show
Mar 15th 2019 | Drew Dillinger & Matt Kenway & Raul LaMotta & The Pizza Guy | def. | Carson Murphy & Corey Roberts & Jimmy Fiasco & Nick King | 8-person tag | |
IWA-MS 899 & Counting
Mar 14th 2019 | Drew Dillinger | def. | Nick Ando | | |
IWA-MS Battle of the Super Juniors
Mar 9th 2019 | Drew Dillinger | def. | The Pizza Guy | | |
IWA-MS Unfinished Business
Dec 4th 2015 | Kevin Lee Davidson | def. | Drew Dillinger | | |
IWA-MS Young Guns Shoot Out
Nov 27th 2015 | Aidan Blackhart | def. | Drew Dillinger | | |
Drew Dillinger