There are 14 words that start with 'penny'.
| penny | pennywise |
| pennywort | pennycress |
| pennyroyal | pennyworth |
| pennyworts | pennyroyals |
| pennyweight | pennyworths |
| pennycresses | pennyweights |
| pennywhistle | pennywhistles |
Note: These 14 words that start with 'penny' are found from the USA & Canada version of the tournament Scrabble word list.