On Sunday night during Super Bowl LVIII, the San Francisco 49ers were leading 10-0, 16-13, 19-16 and 22-19 against the Kansas City Chiefs.

Despite all these advantages, head coach Kyle Shanahan's crew was never able to get any closer and ultimately lost in overtime 25-22.

As Niners fans know, this wasn't the first time the team squandered a golden opportunity to win a sixth Super Bowl title on the biggest stage against the Chiefs with Shanahan at the helm.

As Josh Dubow of the Associated Press noted on Monday, the 44-year-old has already seen three historic Super Bowl losses.

In February 2020, Jimmy Garoppolo's 49ers had a 20-10 lead over the Chiefs late in the third quarter of Super Bowl LIV. Kansas City quarterback Patrick Mahomes helped the team score three goals in the final quarter, and San Francisco's double-digit lead disappeared in the 31-20 final.

This was Shanahan's third season as the group's leader and All-Pro guard Fred Warner, who recently said the loss “scarred him for life.”

Before coming to the Bay Area, Shanahan was the offensive coordinator of the Atlanta Falcons during the 2015 and 2016 campaigns.

Super Bowl LI took place in February 2017, a few months before Mahomes was drafted. This winter, however, Shanahan was tasked with matching five-time Super Bowl MVP Tom Brady, and despite leading 28-3 in the second half, Atlanta notoriously lost in overtime, 34-28.