I've done a more comprehensive search for Hugh Wilson in the database of early Philadelphia Inquirer issues I have access to. I essentially searched for "H I Wilson" or "Hugh Wilson" or "Hugh I Wilson" from 1890 to 1922. Sorting through the many hits I think this is a reasonably complete list of stories where he is mentioned, but I'm sure I missed a few or more. In chronological order:
1. March 1, 1896: youngster at a dinner party (in the 'This Week in Society' article)
2. July 26, 1896: family makes trip to the Adirondacks
3. May 9, 1897: GAP match for Belmont team
4. Dec 4, 1897: GAP tourney
5. Dec 5, 1897: match at Philly CC
6. Mar 6, 1898: story calls him 'king' golfer at Belmont and that he doesn't play when the weather gets cold.
7. May 8, 1898: interclub match playing for Philly CC
8. June 1, 1898: usher at a wedding.
9. Dec 31, 1899: at a 'subscription dance' (?); Mary Warren in attendance too.
10. July 29, 1900: at an 'enchre party' (?) in Spring Lake, NJ
11. Dec 19, 1900: appointed manager of P'ton FR baseball team
12. May 18, 1901: named captain of golf team
13. June 26, 1901: leaves to visit Silver City, NM (I think this is where little mentioned brother Wayne lives).
14. May 11, 1902: NCAA match at Garden City
15. June 14, 1903: better ball tourney
16. oops, I skipped a number!
17. Sept 27, 1903: GAP qualifier
18. Nov 4, 1903: wins Election Day Trophy tourney at St Davids
19. May 8, 1904: interclub match
20. May 26, 1904: Stevenson Cup qualifier (playing for Merion)
21. May 28, 1905: GAP match at HVCC (for Merion)
22. June 4, 1905: GAP match vs Mt. Airy
23. May 24 and July 1, 1906: tourneys at Merion
24. Jan 17, 1907: squash tourney
25. Jan 24, 1907: squash tourney
26. April 21, 1907: named to play in 4/27/07 Chevy Chase match
27. June 29, 1907: a "Hugh Wilson" is listed on a boat to Glasgow.
28. February 12, 1908: squash tourney
29. May 3, 1908: intercity match vs Washington
30. Jan 17, 1909: squash tourney.
31. Feb 16, 1909: squash tourney (defaulted match)
32. March 18, 1909: Princeton Club dinner.
33. Dec 1, 1911: at the Radnor Horse Show (Robert Leslie there too)
34. Sept 12, 1912: tourney invite for 9/27 and 9/28
35. Apr 10, 1913: Cobb's stuff.
36. Apr 25, 1913: Cobb's stuff.
37. June 23, 1913: Philly Cup competition
38. June 24, 1913: upcoming GAP tourney
39. July 5, 1913: GAP match
40. July 6, 1913: GAP match
41. Sept 20, 1913: Lesley Cup qualifier invite.
42. Dec 31, 1913: caddy dinner story at Merion.
43. Nov 4, 1914: Joe Bunker article.
44. Jan 24, 1915: Joe Bunker Cobb's story.
45. March 17, 1915: Joe Bunker article.
46. Apr 9, 1915: 4-ball match w/ Ouimet at Seaview
47. Jan 9, 1916: Joe Bunker Cobb's article.
48. Apr 23, 1916: Joe Bunker article that includes recent changes to Merion for upcoming National Amateur tourney.
49. Jan 14, 1917: Billy Bunker article
50. Mar 11, 1917: his work on two holes at Philmont
51. April 15, 1917: mentioned in part of PV story
52. Apr 22, 1917: Billy Bunker article.
53. Apr 21, 1919: mentioned "In a Social Way" article
54. Dec 21, 1919: part of "Clubs and Clubmen" article where he is mentioned finishing PV
55. Jan 8, 1920: elected to exec comm of USGA
56. Jan 10, 1920: same as above
57. Jan 18, 1920: same as above
58. Feb 8, 1920: trip to Atlantic City
59. Nov 13, 1920: mentioned "In a Social Way" article
60. Nov 4, 1920: again USGA comm mention
61. Dec 1, 1920: sold house in Bryn Mawr
62. Dec 5, 1920: dance invitation at Merion CC
63. Aug 2, 1921: trip to NY
64: Oct 31, 1921: guest at H'ween dance.
65. Mar 3, 1922: searching for more golf course sites for the city