NHL playoff square pools rely on chance rather than skill to decide the winner -- which doesn't mean they aren't entertaining. Draw an 8x8 grid on a sheet of paper, and have participants write their name on one or more squares. Once the grid is filled with names, place the logos of the eight Eastern Conference playoff teams in one hat, and the Western Conference playoff teams in another. Place the first Eastern team drawn atop the first square on the top row, and continue across until each is labeled with a conference team. Place the first Western team drawn to the left of the first square, and continue placing teams on the rows below until the final team left is placed on the bottom row. The winner is the one whose name is on the square that intersects with the two teams that reach the Stanley Cup final.
The traditional playoff bracket involves picking the winner of each playoff series before the competition begins. For years, this was difficult to manage for the Stanley Cup playoffs, because the teams were reseeded after every round, effectively changing the bracket after each series. That changed in 2014, however, so now bracket games are easier to organize. One big challenge is determining how to award points. For example, one point may be awarded for a first-round series picked correctly, two points for a second-round winner, three points for a conference finals winner, and four points for the Stanley Cup champion. The more heavily the late-round series are weighted, the more critical it is to pick the champion correctly.
Another option is to draft teams of individual players and base the pool on their stats. Categories often used for this include goals and assists to track the offensive players, with hits and blocked shots rewarding defensive prowess. This requires participants to balance the skills of the individual players against how far teams are likely to advance -- a second-line center on a championship team easily could provide more goals than the top scorer in the NHL whose team gets bounced in the first round. Award entrants points for how their teams of individual players finish in each statistical category. Determine how many players each team will need and how the selections will be made. You can have player selection be a straight draft, an auction, or have a salary-cap format where each player is assigned a certain dollar figure and entrants must keep their rosters under a specified amount. Track points once the playoffs start and send out the standings on a regular basis.
Keep It Going
The downside of the NHL playoffs for pool purposes is that they last from April to June, meaning that some participants may lose interest if their teams fall to the bottom of the standings. One way to keep things interesting in a player pool is to allow participants to replace players from eliminated teams after each of the first two rounds, picking in standings order from worst to first among the remaining players not already on a pool roster. Another is to add a second, separate competition for the Stanley Cup final, where participants again pick players from the two remaining NHL teams based on the same categories as the original pool.