There are 15 words that start with 'boss'.
| boss | bossy | bossed |
| bosses | bossdom | bossier |
| bossies | bossily | bossing |
| bossism | bossdoms | bossiest |
| bossisms | bossiness | bossinesses |
Note: These 15 words that start with 'boss' are found from the USA & Canada version of the tournament Scrabble word list.