An Oregon native, Derek Maiben was a First-Team All-State player as a senior for Newberg High School. He stayed in the Pacific Northwest, playing five years at Division II’s Western Oregon University from 2019 to 2023.

His freshman year, he was the second-best hitter for the Wolves with a .387 average. He was awarded with First Team D2CCA All-West Region honors. In the shortened 2020 season, he played ten more games.

As a redshirt sophomore in 2021, he hit .400 and led the team with 50 hits over 30 contests. The following year, he was an All-GNAC Honorable Mention and helped lead his school to a conference championship and NCAA West Regional appearance. His final year of school in 2023, the infielder accrued 75 hits in 45 games, totaling a .414 average.

Maiben turned pro in the summer of 2023, playing for the Pioneer League’s Boise Hawks for 57 games. Maiben notched 61 hits, including 13 for extra bases, while driving in 31 runs.

In 2024, he joined the American Association. Over 48 games with Sioux Falls and 22 more games with Chicago, he hit .291 and walked 29 times. Right before Opening Day 2025, he was traded to Lincoln and appeared in seven games for the SaltDogs before he was signed by Fargo-Moorhead. In 25 games for the RedHawks, he hit .277 and stole seven bags.

Now, Lake Country has acquired the infielder in a trade, marking his fifth stop in the Association.