July 1, 1997 Roger Clemens (father of current Jays farm hand Kacy Clemens) on the mound, against some retread who up to that year had been worth less than 0 bWAR, Jeff Juden.
In the first inning. Clemens after retiring the first 2 hitters, including Mark Grudzielanek (uncle to current Jays farm hand Brandon Grudzielanek) gives up a single to FP Santangelo and a double to David Segui, Jays are down 1-0.
2nd inning, Rondell White hits a massive HR of Clemens, and the Jays are done 2-0.
The game would stay like this until the bottom of the 8th inning, when Shawn Green, hits a solo HR off Juden to bring the score 2-1, bringing back the hopes of a significant part of the home crowd.
In the top of the 9th inning, an event that Jays fans will need to get use to for many years to go i hope, Vladimir Guerrero lead of the inning with a hit. Sadly, he was caught stealing 2nd something we can hope his son ,Vladimir Jr is learning not to do, maybe he can learn this in AA before skipping over Buffalo.
The Jays do put a man on in the bottom of the 9th, but future convicted felon, Ugueth Urtain Urbina (hard to believe Roger Clemens was not the biggest jerk involved in this game) came in for the save , making the Jays comeback insufficient, and Roger Clemens a loser.
(as for after 2009, the Reds game in June 2014 would likely be my favourite)