Bret Hart Vs. Shawn Michaels Complete History | Wrestling Timelines

September 11, 1989 - First Interaction

The first in-ring meeting between Bret Hart and Shawn Michaels unfolds when the Hart Foundation of Bret and Jim Neidhart take on the Rockers, who were rehired in May ‘88, on Prime Time Wrestling.

There’s a very interesting moment early on, before Bret ties up with Marty Jannetty. As Bret circles the ring, he refuses to break eye contact with Shawn, who is stationed on the apron. It’s as if Bret knows who the real threat is - that, or he’s slyly expressing his joy at the prospect of grappling with a like-minded workhorse in whom he sees a bit of himself.

The match is good, an awkward Rockers double hip-toss spot aside. It ends when the Rougeaus run in to attack the Rockers, necessitating a disqualification.

The two teams will reach a higher peak.

November 25, 1989 - Better

The fledgling rivalry makes its way to the discerning, taste-making spiritual home of Madison Square Garden - and the fans love it.

The match drags, almost by design - it goes to a 20:00 time limit draw - but it smashes every other thing on the card. The structure will become familiar. Bret partners up with Marty as Neidhart then does spots with Michaels. The idea is to create anticipation for the best pairing, who are tasked with building the match to a scintillating peak - and that pairing is not Neidhart and Jannetty.

Away from the rest holds, there’s a gorgeous cut-off when Shawn practically teleports into Bret’s high boot in the corner. Shawn sells it like a knock-out blow; Hart doesn’t leave so much as a blush on Shawn’s cheek. It’s a captivating glimpse into what they may achieve together in a singles match - but will they ever truly get there?