| Loss | Clay Guida | 155 | UFC 237 - Namajunas vs Andrade | May 11th 2019 | Rio De Janeiro, Brazil | DEC (U) | 3 | 5:00 |  |
| Loss | Ryan Hall | 155 | UFC 232 - Jones vs Gustafsson 2 | Dec 29th 2018 | Inglewood, USA | SUB (heel hook) | 1 | 2:46 | |
| Loss | Dennis Siver | 145 | Fight Night 112 - Chiesa vs Lee | Jun 25th 2017 | Oklahoma City, USA | DEC (M) | 3 | 5:00 | |
| Loss | Yair Rodriguez | 145 | Fight Night 103 - Rodriguez vs Penn | Jan 15th 2017 | Phoenix, USA | TKO | 2 | 0:24 | |
| Loss | Frankie Edgar | 145 | TUF 19 Finale | Jul 6th 2014 | Las Vegas, USA | TKO | 3 | 4:16 | |
| Loss | Rory MacDonald | 170 | UFC on Fox 5 - Henderson vs Diaz | Dec 8th 2012 | Seattle, USA | DEC (U) | 3 | 5:00 | |
| Loss | Nick Diaz | 170 | UFC 137 - Penn vs Diaz | Oct 29th 2011 | Las Vegas, USA | DEC (U) | 3 | 5:00 | |
| Draw | Jon Fitch | 170 | UFC 127 - Penn vs Fitch | Feb 27th 2011 | Sydney, Australia | DEC (M) | 3 | 5:00 | |
| Win | Matt Hughes | 170 | UFC 123 - Rampage vs Machida | Nov 20th 2010 | Auburn Hills, USA | KO | 1 | 0:21 | |
| Loss | Frankie Edgar | 155 | UFC 118 - Edgar vs Penn 2 | Aug 28th 2010 | Boston, USA | DEC (U) | 5 | 5:00 | |
| Loss | Frankie Edgar | 155 | UFC 112 - Invincible | Apr 10th 2010 | Abu Dhabi, UAE | DEC (U) | 5 | 5:00 | |
| Win | Diego Sanchez | 155 | UFC 107 - Penn vs Sanchez | Dec 12th 2009 | Memphis, USA | TKO | 5 | 2:37 | |
| Win | Kenny Florian | 155 | UFC 101 - Declaration | Aug 8th 2009 | Philadelphia, USA | SUB (RNC) | 4 | 3:54 | |
| Loss | Georges St. Pierre | 170 | UFC 94 - St. Pierre vs Penn 2 | Jan 31st 2009 | Las Vegas, USA | TKO | 4 | 5:00 | |
| Win | Sean Sherk | 155 | UFC 84 - Ill Will | May 24th 2008 | Las Vegas, USA | TKO | 3 | 5:00 | |
| Win | Joe Stevenson | 155 | UFC 80 - Rapid Fire | Jan 19th 2008 | Newcastle, UK | SUB (RNC) | 2 | 4:02 | |
| Win | Jens Pulver | 155 | TUF 5 Finale | Jun 23rd 2007 | Las Vegas, USA | SUB (RNC) | 2 | 3:12 | |
| Loss | Matt Hughes | 170 | UFC 63 - Hughes vs Penn 2 | Sep 23rd 2006 | Anaheim, USA | TKO | 3 | 3:53 | |
| Loss | Georges St. Pierre | 170 | UFC 58 - USA vs Canada | Mar 4th 2006 | Las Vegas, USA | DEC (S) | 3 | 5:00 | |
| Win | Renzo Gracie | 190 | K-1 World Grand Prix Hawaii | Jul 29th 2005 | Honolulu, USA | DEC (U) | 3 | 5:00 | |
| Loss | Lyoto Machida | 225 | K-1 - Hero's 1 | Mar 26th 2005 | Saitama, Japan | DEC (U) | 3 | 5:00 | |
| Win | Rodrigo Gracie | 182 | Rumble on the Rock 6 | Nov 20th 2004 | Honolulu, USA | DEC (U) | 3 | 5:00 | |
| Win | Duane Ludwig | 170 | K-1 MMA - Romanex | May 22nd 2004 | Saitama, Japan | SUB (arm-triangle) | 1 | 1:45 | |
| Win | Matt Hughes | 170 | UFC 46 - Supernatural | Jan 31st 2004 | Las Vegas, USA | SUB (RNC) | 1 | 4:39 | |
| Win | Takanori Gomi | 155 | Rumble on the Rock 4 | Oct 10th 2003 | Honolulu, USA | SUB (RNC) | 3 | 2:35 | |
| Draw | Caol Uno | 155 | UFC 41 - Onslaught | Feb 28th 2003 | Atlantic City, USA | DEC | 5 | 5:00 | |
| Win | Matt Serra | 155 | UFC 39 - The Warriors Return | Sep 27th 2002 | Uncasville, USA | DEC (U) | 3 | 5:00 | |
| Win | Paul Creighton | 155 | UFC 37 - High Impact | May 10th 2002 | Bossier City, USA | TKO | 2 | 3:23 | |
| Loss | Jens Pulver | 155 | UFC 35 - Throwdown | Jan 11th 2002 | Uncasville, USA | DEC (M) | 5 | 5:00 | |
| Win | Caol Uno | 155 | UFC 34 - High Voltage | Nov 2nd 2001 | Las Vegas, USA | KO | 1 | 0:11 | |
| Win | Din Thomas | 155 | UFC 32 - Showdown in the Meadowlands | Jun 29th 2001 | East Rutherford, USA | TKO | 1 | 2:42 | |
| Win | Joey Gilbert | 155 | UFC 31 - Locked & Loaded | May 4th 2001 | Atlantic City, USA | TKO | 1 | 4:57 | |
