10 pay-per-view matches Triple H Should Have lost

#9 Triple H vs Kurt Angle- Unforgiven 2000

Kurt should have won... It's true

This was possibly the best feud of the year 2000, largely due to how unexpectedly good it was. Triple H and Kurt Angle worked so well together that they would also feud in 2001, 2002 and now, 18 years later, in 2018.

Kurt Angle was WWE's hottest new star after his late 1999 debut, so they needed to be careful about what wins and losses he needed to take. Things were a little rocky for Kurt for a while after taking in quick squash pay-per-view losses to the Big Show and The Undertaker, but it seemed like this love-triangle feud would be where it turned around. The Angle/Triple H/Stephanie romance would provide many entertaining segments between August and October, which would all seemingly lead to a Kurt Angle PPV win, but that didn't happen.

Allegedly the plan was for Stephanie to turn on Triple H at Unforgiven 2000 and help Kurt score the win but plans changed for whatever reason and instead she would cost Kurt the big one, giving him a 4th big loss to a top star on a PPV within the past few months. This would have halted the career of any other star but fortunately, Kurt would bounce back the following month and lift his first WWE Championship from The Rock at No Mercy.