Kyle Lobstein rose to prominence as a standout left-handed pitcher at Coconino High School in Flagstaff, Arizona. Drafted by the Tampa Bay Rays with the 47th overall pick in 2008, he debuted in 2009 with 14 games for the Low-A Hudson Valley. He progressed to 27 appearances for Single-A Bowling Green the following year and split time between High-A Charlotte and Double-A Montgomery the next. Lobstein returned to Montgomery for the 2012 season, recording an 8-7 record and 4.06 ERA with 129 strikeouts in 144.0 innings pitched.

Kyle was selected by the New York Mets in the 2012 Rule 5 Draft before he was flipped to the Detroit Tigers, where he would split the season with Double-A Erie and Triple-A Toledo with a 13-7 combined record.

Lobstein made his MLB debut on August 23rd, 2014, throwing 5.2 innings of three-run ball against Minnesota. For the rest of the season, he would bounce between MLB and Triple-A and earn his first MLB win on September 7th.

Justin Verlander opened the 2015 season injured, so Lobstein made the major league starting rotation to begin the season. He would collect three more MLB wins in 11 Detroit starts during the season while dealing with a midseason shoulder injury and rehabbing at High-A and Triple-A. In December of 2015, Detroit designated Lobstein for assignment.

Lobstein was traded to the Pittsburgh Pirates and split time between Pittsburgh and Triple-A Indianapolis. Through 14 games with the Pirates, Lobstein recorded a 3.96 ERA over 25 innings On August 30, 2016, Lobstein was traded to the Baltimore Orioles and reported to Triple-A Norfolk where he pitched in one game before their season ended.

He elected free agency and signed a minor league deal with the Miami Marlins. Lobstein split 2017 between Double-A Jacksonville and Triple-A New Orleans posting a cumulative 2.11 ERA with 31 strikeouts in 42.2 innings.

In 2018, Lobstein signed with the Toros de Tijuana of the Mexican Baseball League. Lobstein finished out the Spring Tournament of the season, recording a 4-2 record and a 2.95 ERA across 11 starts before he was released and signed a minor league contract with the Los Angeles Dodgers. He was a combined 4–7 with a 3.79 ERA across 14 starts for Double-A Tulsa and Triple-A Oklahoma City.

After the season, Lobstein signed a minor league contract with the Oakland Athletics. He spent 2019 with Triple-A Las Vegas, registering a 6-4 record and 4.75 ERA in 43 appearances. In December of 2019, Lobstein signed a minor league contract to return to the Dodgers but did not play in 2020 due to the pandemic.

Lobstein signed a minor league contract with the Washington Nationals in 2021. He was assigned to Triple-A Rochester to begin the season and struck out 25 batters in 16 appearances with an impressive 1.69 ERA before being called back up to MLB. After struggling in three appearances with Washington, Lobstein was designated for assignment and traded to the Milwaukee Brewers in exchange for cash considerations and was optioned to Triple-A Nashville.

In March of 2022, he resigned with Tijuana. Lobstein appeared in 13 games, posting a 1-2 record and 5.01 ERA with 31 strikeouts in 23.1 innings pitched.

In early 2023, Lobstein was actually loaned to the Lake Country DockHounds. However, prior to the start of the American Association season, Lobstein’s contract was returned to Tijuana.

The following month, Lobstein signed with the Long Island Ducks of the Atlantic League. In 37 games, including 12 starts, Lobstein pitched to a 5-5 with a 5.66 ERA and 81 strikeouts.

After not playing in 2024, Lobstein makes his Lake Country DockHounds debut two years after initially being loaned.