| Game |
| Result | Moves |
Year |
Event/Locale | Opening |
| 26. Tarrasch vs Pillsbury |
 | 1-0 | 45 |
1898 |
Vienna | C65 Ruy Lopez, Berlin Defense |
| 27. Showalter vs Pillsbury |
 | 0-1 | 25 |
1898 |
Pillsbury - Showalter | C65 Ruy Lopez, Berlin Defense |
| 28. K Walbrodt vs Pillsbury |
 | 0-1 | 32 |
1898 |
Vienna | C65 Ruy Lopez, Berlin Defense |
| 29. Showalter vs Pillsbury |
| 1-0 | 42 |
1898 |
Pillsbury - Showalter | C65 Ruy Lopez, Berlin Defense |
| 30. Tarrasch vs Pillsbury |
 | 1-0 | 41 |
1898 |
Vienna | C67 Ruy Lopez |
| 31. Showalter vs Pillsbury |
| 0-1 | 32 |
1898 |
Pillsbury - Showalter | C67 Ruy Lopez |
| 32. Tinsley vs Pillsbury |
| 0-1 | 55 |
1899 |
London | C67 Ruy Lopez |
| 33. J F Barry vs Pillsbury |
 | 1-0 | 44 |
1899 |
Boston m | C65 Ruy Lopez, Berlin Defense |
| 34. Showalter vs Pillsbury |
| ½-½ | 44 |
1899 |
Exhibition Match | C67 Ruy Lopez |
| 35. Didier vs Pillsbury |
 | 0-1 | 29 |
1900 |
Paris | C67 Ruy Lopez |
| 36. H Wolf vs Pillsbury |
| 0-1 | 40 |
1900 |
Munich | C67 Ruy Lopez |
| 37. Showalter vs Pillsbury |
| ½-½ | 45 |
1900 |
Paris | C67 Ruy Lopez |
| 38. Maroczy vs Pillsbury |
 | ½-½ | 58 |
1900 |
Munich | C67 Ruy Lopez |
| 39. Schlechter vs Pillsbury |
| ½-½ | 45 |
1900 |
Munich | C79 Ruy Lopez, Steinitz Defense Deferred |
| 40. Schlechter vs Pillsbury |
 | 0-1 | 56 |
1900 |
Munich | C79 Ruy Lopez, Steinitz Defense Deferred |
| 41. Halprin vs Pillsbury |
 | ½-½ | 24 |
1900 |
Munich | C67 Ruy Lopez |
| 42. L C Karpinski vs Pillsbury |
| 0-1 | 39 |
1901 |
Buffalo | C88 Ruy Lopez |
| 43. W Napier vs Pillsbury |
| 0-1 | 35 |
1901 |
Buffalo | C84 Ruy Lopez, Closed |
| 44. G Marco vs Pillsbury |
 | 1-0 | 52 |
1902 |
Monte Carlo | C67 Ruy Lopez |
| 45. H E Atkins vs Pillsbury |
 | 0-1 | 42 |
1902 |
13th DSB Kongress (Hanover) | C65 Ruy Lopez, Berlin Defense |
| 46. Teichmann vs Pillsbury |
| ½-½ | 41 |
1902 |
Monte Carlo | C67 Ruy Lopez |
| 47. Von Bardeleben vs Pillsbury |
| 0-1 | 48 |
1902 |
13th DSB Kongress (Hanover) | C77 Ruy Lopez |
| 48. Gunsberg vs Pillsbury |
| ½-½ | 41 |
1902 |
Monte Carlo | C79 Ruy Lopez, Steinitz Defense Deferred |
| 49. H Wolf vs Pillsbury |
| ½-½ | 51 |
1902 |
Monte Carlo | C67 Ruy Lopez |
| 50. G Marco vs Pillsbury |
| ½-½ | 42 |
1903 |
Monte Carlo | C67 Ruy Lopez |