The HMWL Champinship is one of great history, incredible games, and legendary players. It all started in 2001, with the League2k1 Championship. There, on the right shoulder of Rich McMackin, the team of Matt Cassaro & Rich McMackin easily disposed of Justin Hastings and rookie Matt Lincoln in a 7-2 affair. In the game, McMackin commanded his pitches in every single sticky situation. Hastings & Lincoln could never come up with a clutch hit. After two homers in the fifth inning by McMackin, it was all but over. McMackin & Cassaro had been crowned the league's first ever champions.

In 2002, it was a bit of a different story. As any HMWL player will tell you, the 2002 season of Wiff 2.0 was the greatest the HMWL has ever seen. And the championship game did not disappoint. After a heated battle between the team of Rich McMackin & Fred Rogers against Justin Hastings & Matt Cassaro became tied up several times, Fred Rogers, then a rookie, ended the game with one single blow.
In the home half of the sixth, after Matt Cassaro had mowed down Rich McMackin, Rogers stepped to the plate. The rest is history. A single swing deposited a Cassaro offering into right field. McMackin & Rogers were Wiff 2.0 champions.

After an off-year in 2003, the HMWL Championship returned in 2004. Arriving months after the end of the regular season, Craig Hastings & Fred Rogers hosted Will Kenney & Justin Hastings in a game of epic proportions. Hastings & Kenney miraculously scored three runs in the top half of the sixth, tying the game at four and sending it into extras. Two innings later, Craig Hastings stepped to the plate with a championship and HMWL history on his mind. Just like Rogers in '02, Hastings calmly hit a walk-off job to right field, making for another legendary ending to an HMWL season.