Jackass
Award #1

Shea's Funky Bunch
Attempt to start Isaac Bruce during
Bye-Week(2)

Journeyman
Award

Germane Crowell
Li'l C's traded Week 2 to Funky Bunch, Funky Bunch traded
Week 3 to MeanGuys

Jackass
Award #2

The Kamakazes
Attempt to start Keith Poole during
Bye-Week(3)

Longevity
Award

Terry Hardy
Picked-Up 9/30/99, Dropped 10/1/99 by The Kamakazes

Lucky Jackass
Award #1

The Guinea
Attempt to start Pete Stoyanovich during Bye Week(6), and still won.

Dumb-Shit
Award #1

Easy Money
Attempt to Pick-Up Mike Vanderjagt when he's not a Free Agent

Dumb-Shit
Award #2

The Scrumps
Attempt to Pick-Up Gary Brown when he's not a Free Agent

Fuckin' Smarten Up Award

Head-Slap
Did not submit a tie-breaker player and lost for that reason for the second time