| # | Name | Term Start | Term End | # of Terms | Party |
|---|---|---|---|---|---|
| 1 | Frederick Allen | 1595 | 1598 | 1 | N/A |
| 2 | Daniel Webster (1st Term) | 1598 | 1601 | 1 | N/A |
| 3 | Alex Drumpf | 1601 | 1604 | 1 | N/A |
| (2) | Daniel Webster (2nd Term) † | 1604 | 1604 | Partial | N/A |
| - | Vacant | 1604 | 1605 | - | - |
| 4 | Dorian Fowler | 1605 | 1610 | 1 1/2 | N/A |
| 5 | Thomas Washington | 1610 | 1616 | 2 | N/A |
| 6 | Anthony Franklin (1st Term) | 1616 | 1619 | 1 | N/A |
| 7 | Benjamin Harris (1st Term) | 1619 | 1625 | 1 | N/A |
| (6) | Anthony Franklin (2nd Term) | 1625 | 1630 | 1 | Labour |
| (7) | Benjamin Harris (2nd Term) | 1630 | 1635 | 1 | Feudalist |
| 8 | Harold Sowers | 1635 | 1650 | 3 | Labour |
| 9 | Derrick Dimitri | 1650 | 1660 | 2 | Labour |
† - The mayor died in office that term