Sir Gregory Penwood is a minor character in the Hellsing manga and the OVAs. He is the grandson of Sir Shelby M. Penwood, following in his ancestor's footsteps by becoming a member of The Convention of Twelve. He makes a brief appearance in the final chapter of Volume 10.
Sir Gregory Penwood seems to be as hesitant as his grandfather, if somewhat shy and slightly petulant.
Thirty years after the Battle of London and Alucard's disappearance, Sir Gregory was practicing his fencing with Sir Integra Fairbrook Wingates Hellsing. He complimented Integra's skill after she defeated him, only for the Hellsing leader to reply that he strongly reminded her of his grandfather.
When Gregory asked Integra to tell him about his grandfather, she spun a wild tale of Shelby M. Penwood as a fearless warrior who singlehandedly turned the tide against Millennium and that she'd lost her left eye during a fencing match with him once.
Gregory was highly skeptical, but Integra insisted that she spoke the truth. Just before she asked him to pay for a new helicopter, which prompted him to leave in tears.