How to Run a Fantasy Baseball League with Friends: The Ultimate Guide

Fantasy baseball isn’t just about the sport—it’s about the friendships, rivalries, and bragging rights that come with managing your own league. Whether you’re playing with coworkers, old college buddies, or family members scattered across Canada, running a league on Pick-PlayFantasy is a great way to stay connected and make the long season even more fun.

Here’s everything you need to know to start and run a successful league with friends.

Step 1: Choose Your League Format

Pick-PlayFantasy offers several ways to play:

  • Head-to-Head (H2H): Compete weekly against one other team in matchups. This is great for friendly rivalries and keeps everyone engaged week to week.
  • Rotisserie (Roto): Teams accumulate stats over the full season, with standings based on cumulative totals. Best for hardcore stat lovers.
  • Points-Based: Players earn points for specific actions (hits, home runs, strikeouts, etc.). This format is simple and fun for newer players.

Tip: If your league includes fantasy newcomers, go with Points or H2H—it keeps things easy and fun.

Step 2: Customize the Rules

Part of the fun of running your own league is tailoring it to your group. You can adjust:

  • Roster size
  • Scoring categories
  • Trade rules
  • Waiver systems
  • Injured list policies

Some leagues even add custom bonuses like “Canadian Player Points” for those who want to spotlight homegrown talent.

Step 3: Plan the Draft Day

This is the most exciting day of the season. Whether you do it online or gather in person over pizza and drinks, make it an event. Consider using a snake draft format (most fair) or auction style for extra strategy.

Encourage everyone to bring a draft board or cheat sheet—and don’t forget to trash talk a little.

Step 4: Keep the League Active

A successful league stays alive throughout the season. Here’s how to keep people engaged:

  • Post weekly updates or power rankings
  • Create a group chat or Discord server
  • Run side competitions (e.g., best weekly score)
  • Schedule mid-season trades and “rivalry week” showdowns

Fantasy is more fun when everyone stays involved, so make interaction part of the experience.

Step 5: End the Season Right

When playoffs hit (or the season wraps in Roto format), make sure to celebrate the winners—and roast the losers. Consider giving out small prizes, trophies, or even just digital badges via the platform. And don’t forget to set a date for next year’s draft. The best leagues last for years.

Bonus Tip: Pick-PlayFantasy makes it easy to archive leagues and carry them into next season. You can even track career records and championship histories for ultimate bragging rights.