| Game |
| Result | Moves |
Year |
Event/Locale | Opening |
| 1. Pillsbury vs Burn |
  | 1-0 | 28 |
1895 |
Hastings | D55 Queen's Gambit Declined |
| 2. Pillsbury vs Tarrasch |
 | 1-0 | 52 |
1895 |
Hastings | D63 Queen's Gambit Declined, Orthodox Defense |
| 3. Pillsbury vs Tinsley |
 | 1-0 | 71 |
1895 |
Hastings | D52 Queen's Gambit Declined |
| 4. Pillsbury vs Schlechter |
  | 0-1 | 44 |
1895 |
Hastings | D53 Queen's Gambit Declined |
| 5. Pillsbury vs J Mason |
  | 1-0 | 36 |
1895 |
Hastings | D53 Queen's Gambit Declined |
| 6. Pillsbury vs Steinitz |
 | 1-0 | 53 |
1895 |
Hastings | D50 Queen's Gambit Declined |
| 7. Pillsbury vs Englisch |
| ½-½ | 62 |
1896 |
Vienna m | D63 Queen's Gambit Declined, Orthodox Defense |
| 8. Pillsbury vs Lasker |
 | 0-1 | 30 |
1896 |
St. Petersburg 1895-96 | D50 Queen's Gambit Declined |
| 9. Pillsbury vs K Walbrodt |
 | 1-0 | 42 |
1896 |
Budapest | D53 Queen's Gambit Declined |
| 10. Pillsbury vs Maroczy |
 | 1-0 | 47 |
1896 |
Budapest | D55 Queen's Gambit Declined |
| 11. Pillsbury vs Janowski |
 | ½-½ | 78 |
1896 |
Budapest | D50 Queen's Gambit Declined |
| 12. Pillsbury vs Englisch |
| ½-½ | 48 |
1896 |
Vienna m | D53 Queen's Gambit Declined |
| 13. Pillsbury vs E Schallopp |
 | 1-0 | 48 |
1896 |
Nuremberg | D53 Queen's Gambit Declined |
| 14. Pillsbury vs Showalter |
 | 0-1 | 91 |
1897 |
Pillsbury - Showalter | D68 Queen's Gambit Declined, Orthodox Defense, Classical |
| 15. Pillsbury vs Showalter |
 | 1-0 | 66 |
1897 |
Pillsbury - Showalter | D63 Queen's Gambit Declined, Orthodox Defense |
| 16. Pillsbury vs Showalter |
 | 1-0 | 40 |
1897 |
Pillsbury - Showalter | D63 Queen's Gambit Declined, Orthodox Defense |
| 17. Pillsbury vs Showalter |
 | ½-½ | 47 |
1897 |
Pillsbury - Showalter | D63 Queen's Gambit Declined, Orthodox Defense |
| 18. Pillsbury vs Showalter |
 | 0-1 | 53 |
1897 |
Pillsbury - Showalter | D66 Queen's Gambit Declined, Orthodox Defense, Bd3 line |
| 19. Pillsbury vs Schiffers |
 | 1-0 | 45 |
1898 |
Vienna | D55 Queen's Gambit Declined |
| 20. Pillsbury vs Showalter |
 | 1-0 | 54 |
1898 |
Pillsbury - Showalter | D60 Queen's Gambit Declined, Orthodox Defense |
| 21. Pillsbury vs Blackburne |
  | ½-½ | 81 |
1898 |
3rd Anglo-American Cable Match | D63 Queen's Gambit Declined, Orthodox Defense |
| 22. Pillsbury vs Showalter |
| 1-0 | 48 |
1898 |
Pillsbury - Showalter | D60 Queen's Gambit Declined, Orthodox Defense |
| 23. Pillsbury vs H W Trenchard |
 | 1-0 | 26 |
1898 |
Vienna | D60 Queen's Gambit Declined, Orthodox Defense |
| 24. Pillsbury vs Lipke |
| ½-½ | 58 |
1898 |
Vienna | D60 Queen's Gambit Declined, Orthodox Defense |
| 25. Pillsbury vs Showalter |
| ½-½ | 73 |
1898 |
Vienna | D63 Queen's Gambit Declined, Orthodox Defense |