Despite being a hard taskmaster, "Woody", as he is occasionally affectionately known, appears to have a softer side. He allowed Barnaby to attempt to convince James to be a better player instead of forcing James after his mental-draining incident, and despite James' inability to follow orders kept him as a reserve.
He begrudgingly allowed Layla to try out for the boys rugby team after Barnaby pointed out that there was nothing forbidding girls from joining in the rules. After Layla performed poorly initially, and later threw Ned Phillips across the pitch, Mr. Woodbridge ordered her off the pitch and forbade her from joining the team.
He is known to become exacerbated when students come seeking romantic advice, especially when they have a crush on Barnaby. Nonetheless, he has a largely laissez-faire attitude about relationships between his players, and dislikes encouraging or discouraging anything. He has gotten especially annoyed with team members asking for advice on having a crush one Barnaby.
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He asks the Art department to let Barnaby into the art rooms after James' death. They gave Barnaby a key.