Inheriting a program that was 1–24 before he took over, Engelstad led the Mountaineers to a 16–10 overall record, including wins over a nationally ranked
Williams featuring
Duncan Robinson.
[4]The following season, Engelstad guided Southern Vermont to a
NECC regular season title, its best record in program history with a 25–4 record, and its first-ever appearance in the
ECAC Division III New England Basketball tournament, capturing the school's first ECAC title of any kind.
[5]
The following season, Southern Vermont won both the NECC regular season and tournament title with a perfect 16–0 mark in conference play, and a 24–4 overall record en route to the school's second-ever NCAA Tournament appearance.
[6]Following a 17–10 overall record in the 2016–17 season and another NECC regular season title, Engelstad coached the Mountaineers to its fourth-straight NECC regular season title, its second conference tournament title and an appearance in the
2018 NCAA Division III tournament. With a 104–34 overall record in five seasons, Engelstad is the all-time wins leader in Southern Vermont basketball history