2009-10: Jordan Oesterle skated for the Belle Tire U18 midget team in Michigan. He was selected by Sioux Falls in the second round (26th overall) of the 2010 USHL Entry Draft.
2010-11: Oesterle played in 54 of 60 games for Sioux Falls in his first USHL season. He scored 2 goals with 13 assists and was +8 with 16 penalty minutes. The Stampede finished third in the Western Conference and reached the Clark Cup playoff semifinals; falling to eventual champion Dubuque. Oesterle scored 2 goals with 3 assists and was +2 in 10 playoff games. In December he committed to playing college hockey at Western Michigan in 2011-12.
2011-12: Oesterle skated in all 41 games for Western Michigan in his freshman season. He scored 2 goals with 6 assists and was +2 with 8 penalty minutes. Western Michigan won the CCHA's playoff title after finishing tied for second in the regular season; earning a berth in the NCAA West Regional. The Broncos lost to North Dakota, 3-1, in the NCAA West semifinals.
2012-13: Oesterle played in all 38 games in his sophomore season on a Western Michigan defense corps that featured future Detroit Red Wing Dan DeKeyser, Tampa Bay prospect Luke Witkowski, and exciting freshman Kenny Morrison. He scored 3 goals with 6 assists and was +7 with 14 penalty minutes. Western Michigan finished third in the CCHA in the conference's final season but did not receive an NCAA at-large bid after losing to Michigan in the conference quarterfinals.
2013-14: Oesterle made his professional hockey debut with the Oklahoma City Barons after signing a two-year entry-level contract with Edmonton in March following his junior season at Western Michigan. He scored one goal with four assists and was -3 with 2 penalty minutes in four regular season games for the Barons. Oesterle scored 2 goals with 15 assists and was an even plus/minus with 27 penalty minutes in 34 games for Western Michigan. The Broncos finished tied with Minnesota-Duluth for fourth place in the new NCHC conference and reached the playoff semifinals; falling to Denver and then losing 5-0 to North Dakota in the league's third-place game.
Edmonton signed Oesterle to a two-year entry-level contract on March 31st, 2014.