5 SEG era UFC fights that never happened

#2) UFC Hall of Famer Don Frye vs. UFC Hall of Famer Bas Rutten

(L) Don Frye - @83weeks IG (R) @basruttenmma IG

Despite competing in the same era, Don Frye and Bas Rutten’s paths never crossed in the UFC. Frye began his career in the promotion’s early years and won two out of the three tournaments he competed in. Rutten on the other hand, competed in the Japanese-based Pancrase promotion where he was the reigning King of Pancrase champion.

In 1997, ‘The Predator’ took a break from MMA in favor of a move to New Japan Pro Wrestling. Meanwhile, ‘El Guapo’ joined the promotion in 1999, so their paths never crossed in the cage. If Frye returned in 1999, he could’ve fought Rutten for the then vacant heavyweight championship.

Based on their respective fighting styles, a bout between the two could’ve gone down as a classic slugfest. ‘El Guapo’ would’ve had a slight advantage with his kicks and submissions, but ‘The Predator’ proved to be a tough fighter to put away throughout his career.

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#1) UFC Hall of Famer Chuck Liddell vs. Frank Shamrock

(L) Frank Shamrock @frankshamrockhalloffame IG (R) Chuck Liddell - @whosinyourcorner IG

UFC Hall of Famer Chuck Liddell and former light heavyweight champion Frank Shamrock could’ve been very lucrative for the promotion.

Shamrock trained out of his brother Ken’s famous ‘Lion’s Den’ and quickly became one of the top fighters in the sport. He represented a new era of fighters as he was well-rounded in all aspects of MMA. Liddell was also important as he eventually became a mainstream star that helped propel the promotion to new heights on pay-per-view.

‘The Iceman’ and Shamrock joined the promotion a few months apart, but the ‘Lion’s Den’ member was much more experienced. He became the inaugural light heavyweight champion and had four title defenses. However, Shamrock vacated the title and left the promotion after defeating Tito Ortiz, so a bout with Liddell never happened. ‘The Iceman’ had an impressive start to his career and a title fight with Shamrock could have eventually taken place.