What a roller coaster ride the last nine years of Michigan Football have been. Former U-M head coach Jim Harbaugh returned to Ann Arbor back in 2015, and the belief was that a national championship would soon follow. Although Harbaugh would ultimately deliver on those lofty expectations in year nine, the reality is that the journey to winning the CFP 2024 National Championship was much longer (and far more painful) than most expected.

At the conclusion of Michigan’s awful 2-4 record during the COVID season in 2020, there were real questions about whether or not Harbaugh would return for his sixth year as head coach of the Wolverines. At that point in time, Harbaugh’s record against Ohio State was a dismal 0-5, and his postseason bowl record of 1-4 wasn’t much better. Although the Wolverines had achieved three 10-win seasons during Harbaugh’s first six years, there was a growing belief that Michigan had reached its ceiling with Harbaugh running things in Ann Arbor.

As it turns out, the fans who believed that – and there were plenty of them – couldn’t have been more wrong.

The beginning of the 2021 season would represent a turning point for Harbaugh and the Michigan Wolverines, one that set the stage for an incredible run over the next three seasons. Michigan fans would experience three consecutive wins over Ohio State, three consecutive Big Ten Championships, and a National Championship from 2021-23 – arguably the greatest three-year stretch in Michigan Football history.

Given how incredible the ride has been over the last nine seasons, I thought it would be interesting to take a look back at some of the most painful losses and enjoyable wins from the Jim Harbaugh era.

Here are the top five for each:

Most Painful Losses

5. No. 16 Michigan at No. 7 Penn State – 2019

4. No. 3 Michigan at Iowa – 2016

3. No. 2 Michigan vs. No. 3 TCU – 2023 Fiesta Bowl

2. No. 3 Michigan at No. 2 Ohio State – 2016

1. No. 12 Michigan vs. No. 7 Michigan State – 2015

Most Enjoyable Wins

5. No. 3 Michigan vs. No. 2 Ohio State – 2023

4. No. 1 Michigan vs. No. 2 Washington, 2024 National Championship

3. No. 3 Michigan at No. 2 Ohio State – 2022

2. No. 5 Michigan vs. No. 2 Ohio State – 2021

1. No. 1 Michigan vs. No. 4 Alabama – 2024 Rose Bowl

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