| card/ date | match | match type | title(s) |
|---|
 IWA-MS Egg Suckin Dog Days of Summer 2019
Jun 27th 2019 | Jimmy Jacobs | def. | Dewey Wellington | Loser Leaves IWA Mid-South | |
IWA-MS The Dirty
May 30th 2019 | Jimmy Jacobs | def. | Dewey Wellington | | |
IWA-MS Payback, Pain & Agony 2019
May 23rd 2019 | Brayden Lee | def. | Aidan Blackhart, Alexander Knight, Amazing Maria, Christian Kobain, Crash Jaxon, Dewey Wellington, Eye Candy Elliott, Lukas Jacobs, Mo Atlas, Tony Evans | Rumble | |
IWA-MS Mayhem In May
May 16th 2019 | Kevin Giza | def. | Adam Slade, Dewey Wellington, Joshie Boy, Lukas Jacobs, Steve Manders | Opportunity in a Box Ladder Match | |
IWA-MS Somebody's Gonna Hurt Somebody 2019
May 9th 2019 | Big Cuz | def. | Dewey Wellington, Joshie Boy, Lukas Jacobs | four-way | |
IWA-MS Derby Madness 2019
May 2nd 2019 | Aaron Williams (c) | def. | Dewey Wellington | | IWA:MS Junior Heavyweight Title
|
IWA-MS Spring Tryout Show 2019
Apr 25th 2019 | Dewey Wellington | def. | Joshie Boy | | |
IWA-MS We Are IWA 2019
Apr 18th 2019 | Joe Travis | def. | Brayden Lee, Dewey Wellington, Kevin Giza, Logan James, Lukas Jacobs | 6-way scramble | |
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 | Dewey Wellington | def. | Raul LaMotta | | |
IWA-MS Legendary
Mar 28th 2019 | Drew Dillinger | def. | Dewey Wellington | | |
IWA-MS 900th Show
Mar 15th 2019 | Jimmy Jacobs | def. | Dewey Wellington | | |
IWA-MS 899 & Counting
Mar 14th 2019 | Dewey Wellington | def. | Ryan Cassidy | | |
IWA-MS Battle of the Super Juniors
Mar 9th 2019 | Kevin Giza | def. | Dewey Wellington | | |
IWA-MS Up Against It
Mar 7th 2019 | Dewey Wellington | def. | AKIRA, Jordan Kage | three-way | |
IWA-MS In Like A Lion 2019
Mar 2nd 2019 | Zachary Dayton Pittman (c) | def. | Dewey Wellington | | Grindhouse Pro Title
|
IWA-MS The Heartbreak Ends
Feb 28th 2019 | Dewey Wellington | def. | Sage Philips | | |
IWA-MS Heartbreak After Heartbreak
Feb 21st 2019 | Aaron Williams (c) | def. | Dewey Wellington | | IWA:MS Heavyweight Title
|
IWA-MS Heartbreak After Heartbreak
Feb 21st 2019 | Dewey Wellington | def. | Aidan Blackhart, Austin Rourke, Carlo Vice, Chase Holliday, Corey Roberts, Jordan Kage, Kody Lane, Nick King, Ray Waddell, Sage Cainan, Shain Bender, Shane Sabre | Opportunity in a Box Ladder Match | |
IWA-MS Heartbreak 2019
Feb 15th 2019 | Dewey Wellington | def. | Ace Jackson | | |
IWA-MS Headed for a Heartbreak
Feb 7th 2019 | Logan James | def. | Dewey Wellington | | |
IWA-MS The War to Settle All the Scores
Feb 2nd 2019 | Joe Trigga Travis (c) & Joshie Boy (c) | def. | Biff Wellington III & Dewey Wellington | | IWA:MS Tag Team Titles
|
IWA-MS Winter Armageddon
Jan 31st 2019 | Dewey Wellington | def. | Shain Bender | | |
IWA-MS Lucky 888
Jan 24th 2019 | Dewey Wellington | def. | Steve Manders | | |
IWA-MS Winter Wars 2019
Jan 17th 2019 | Dewey Wellington | def. | Teddy King | 2 out of 3 falls | |
IWA-MS Out With the Old In With the New 2019
Jan 10th 2019 | Dewey Wellington | def. | Teddy King | | |
IWA-MS RassleKingdom
Jan 3rd 2019 | Dewey Wellington | def. | PB Smooth | | |
Dewey Wellington during 2019