Although a draper like his father, Underwood is likely to have dealt in other commodities besides cloth. In 1440, for example, he was engaged in a lawsuit at Westminster against a husbandman from Bedford to whom he claimed to have entrusted ten quarters of malt for safe-keeping nearly 18 years earlier.
Underwood served part of the first of his three known terms as bailiff while a sitting MP. During the second of these terms, he and his co-bailiff, Andrew Rolman, quarrelled with a fellow burgess, John Haukyns, probably in pursuit of their official duties. Hawkyns responded by bringing lawsuits against them at Westminster. Claiming that they had held him a prisoner at Bedford until he paid 40s., he also accused them of breaking into a house of his in the town and of driving away its occupant, one of his tenants.
