Jack Dempsey has six losses against four opponents on his boxing record. For a list of Dempsey's best fights, refer to "Best fights of Jack Dempsey".
On September 22, 1927 Jack Dempsey fought Gene Tunney in a heavyweight world-title fight for Tunney's The Ring title. Dempsey was 32 years old and with a record of 58-6-9 (43), and Tunney was 30 years old and with a record of 77-1-4 (47). Dempsey lost the fight via 10-round unanimous decision.
On September 23, 1926 Jack Dempsey met Gene Tunney in a heavyweight (The Ring) world-title defense fight. Dempsey was 31 years old and with a record of 57-5-9 (42), and Tunney was 29 years old and with a record of 76-1-4 (47). Dempsey lost the fight via 10-round unanimous decision and lost the title.
On September 13, 1918 Jack Dempsey faced off against Willie Meehan at age 23. He was coming in with a record of 45-4-9 (32). Dempsey lost the fight via 4-round points decision.
On March 28, 1917 Jack Dempsey faced off against Willie Meehan at age 21. He was coming in with a record of 26-3-6 (19). Dempsey lost the fight via 4-round points decision.
On February 13, 1917 Jack Dempsey faced off against Fireman Jim Flynn at age 21. He was coming in with a record of 26-2-5 (19). Dempsey lost the fight via 1st-round KO.
On April 5, 1915 Jack Dempsey faced off against Jack Downey at age 19. He was coming in with a record of 5-1-1 (5). Dempsey lost the fight via 4-round points decision.