PB Boss is a user-friendly system that sets up partners and opponents for a Pickleball sessions, eliminating the need for paper charts. 1) create one or more Pickleball clubs 2) add members to the club 3) start a Pickleball session 4) pick players for that Pickleball session 4) PB Boss will schedule 12 Pickleball matches based on the players added for that season. PB Boss also has a Pickleball session attendance reporting function.