| card/ date | match | match type | title(s) |
|---|
 CHIKARA Deuces Wild
Apr 19th 2008 | Gran Akuma | def. | Jimmy Olsen | | |
CHIKARA King of Trios '08: Night 1
Feb 29th 2008 | Cheech & Cloudy & M.C. KZ | def. | Brodie Lee & Jimmy Olsen & Retail Dragon | 6-person tag | |
CHIKARA Two Eyebrows Are Better Than One
Jan 27th 2008 | Sabian | def. | Jimmy Olsen | | |
CHIKARA Battle Of Who Could Care Less
Nov 16th 2007 | El Pantera & Lince Dorado | def. | Colin Olsen & Jimmy Olsen | | |
CHIKARA New Star Navigation
Oct 27th 2007 | Cheech & Cloudy | def. | Colin Olsen & Jimmy Olsen | | |
CHIKARA Bruised
Oct 26th 2007 | Fire Ant & Soldier Ant & Worker Ant | def. | Brodie Lee & Colin Olsen & Jimmy Olsen | 6-person tag | |
CHIKARA Cibernetico & Robin
Sep 22nd 2007 | Cheech & Cloudy | def. | Colin Olsen & Jimmy Olsen | | |
CHIKARA Here Comes the International Invaders: 2nd Stage - Revenge of the Clone Menace
Aug 18th 2007 | Jigsaw & Shane Storm | def. | Colin Olsen & Jimmy Olsen | | |
CHIKARA Here Comes the International Invaders: 1st Stage - Attack of the Phantom Sith
Aug 17th 2007 | Brodie Lee & Colin Olsen & Jimmy Olsen | def. | Fire Ant & Soldier Ant & Worker Ant | 6-person tag | |
CHIKARA Showdown in CrisisLand
Jul 21st 2007 | El Hijo del Ice Cream & Ice Cream Jr. | def. | Colin Olsen & Jimmy Olsen | | |
CHIKARA Young Lions Cup '07 - Day 3
Jun 24th 2007 | Colin Olsen & Jimmy Olsen | def. | Darin Corbin & Ryan Cruz | | |
CHIKARA Anniversario!
May 27th 2007 | Hydra & Ultramantis Black | def. | Colin Olsen & Jimmy Olsen | | |
CHIKARA Anniversario?
May 26th 2007 | Fire Ant & Soldier Ant | def. | Colin Olsen & Jimmy Olsen | | |
CHIKARA Time Will Prove Everything
Mar 24th 2007 | Jigsaw & Shane Storm | def. | Colin Olsen & Jimmy Olsen | | |
CHIKARA King of Trios '07: Night 3
Feb 18th 2007 | Cheech & Cloudy | def. | Jagged & Shane Matthews, American Balloon & Danshoku Dino, Chris Bosh & Scott Lost, Jason Gory & Shiima Xion, Create-A-Wrestler & Player Uno, Equinox & Fire Ant, Excalibur & Joey Ryan, Larry Sweeney & Sharecropper, Mitch Ryder & Robbie Ellis, Soldier Ant & Worker Ant, Brandon Thomaselli & Vito Thomaselli, J. C. Ryder & Lucky, Colin Olsen & Jimmy Olsen, Hydra & Ultramantis Black, Darkness Crabtree & Dr. Cheung, Dunn & Marcos | tag team gauntlet | |
CHIKARA King of Trios '07: Night 2
Feb 17th 2007 | Miyawaki & Yoshiaki Yago | def. | Colin Olsen & Jimmy Olsen | | |
CHIKARA From Zero To Hero (& Castagnoli)
Nov 12th 2006 | Cheech & Cloudy | def. | Colin Olsen & Jimmy Olsen | | |
CHIKARA matches wrestled by Jimmy Olsen