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Askren had a dominant Junior season in 2005–06, winning all 45 of his matches and pinning in 25 of them. He won the 174 pound weight class easily at both the Big 12 and NCAA Championships. He won his Big 12 finals match 17–6 over Jacob Klein of Nebraska and his NCAA finals match 14–2 over future two time NCAA champion, Dan Hodge Trophy winner, and World silver medalist Jake Herbert of Northwestern. Herbert was also undefeated going into the NCAA finals.