Here is a list of O'Brien's best fights. For a list of O'Brien's losses, refer to "Jake O'Brien Losses".
On August 17, 2006 Jake O'Brien faced off against Kristof Midoux at age 21. He was coming in with a record of 8-0 (7). O'Brien stopped Kristof Midoux via TKO.
On November 18, 2006 Jake O'Brien faced off against Josh Schockman at age 22. He was coming in with a record of 9-0 (7). O'Brien won the fight via 3-round unanimous decision.
On January 31, 2009 Jake O'Brien faced off against Christian Wellisch in a light-heavyweight bout at age 24. He was coming in with a record of 11-2 (7), and Wellisch was 33 years old and with a record of 8-4 (7). O'Brien won the fight via 3-round split decision.
On January 25, 2007 Jake O'Brien faced off against Heath Herring at age 22. He was coming in with a record of 10-0 (7), and Herring was 28 years old and with a record of 26-11 (23). O'Brien won the fight via 3-round unanimous decision.
On March 17, 2006 Jake O'Brien faced off against Jay White at age 21. He was coming in with a record of 5-0 (5). O'Brien stopped Jay White via KO.