[5] College Park, Georgia-native Jenkins, was invited to Norcross, Georgia to participate in the December 20–22 eight-man USTA wild card playoff for a spot in the main draw of the 2014 Australian Open.

The field also included defending wild card playoff champion Rhyne Williams, Denis Kudla, Steve Johnson, Tennys Sandgren, Austin Krajicek, Bjorn Fratangelo, and Chase Buchanan.

On September 20, Jenkins made tennis blooper highlights when he failed to execute the second half of an over and back double net jump.

On September 21, the Costa Mesa Pro Classic became his fourth tournament championship as he defeated Dennis Novikov in straight sets in the finals after dispatching Daniel Manlow, Gregory Oullette, Clay Thompson, and Tennys Sandgren along the way.

[12] In the Hutchinson Builders Toowoomba International final (Australia F8 Futures Tournament) the following week, Jenkins was nearly ousted in the first round when he fell behind 0–5 in the third set and faced a match point against Lawrence Bataljin.

Jenkins prevailed 7–5 in that set and went on to win the tournament against top seeded Luke Saville who was returning from a two-month injury layoff.

[14] Jenkins advanced to the finals of the tournament against Bradley Klahn despite enduring a cut wrist at a key point in the semifinals before bowing out as runner-up.

[15][16] Jenkins' hot streak ended the following week when he was eliminated in the 2nd round by Luke Saville at the 2014 Latrobe City Traralgon ATP Challenger 2.

[20] In the 2015 Australian Open – Men's singles qualifying, Jenkins defeated Rajeev Ram[21] and Marco Cecchinato[22] before losing to Tim Pütz.