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| Rk | Year | Tm | Lg | G | W | L | Ties | Finish | Playoffs | R | RA | BatAge | PitchAge | #Bat | #Pitch | Top Player | Managers | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | 1899 | Baltimore Orioles | NL | 152 | 86 | 62 | 4 | .581 | 4th of 12 | 827 | 691 | 27.1 | 26.1 | 24 | 7 | J.McGraw (8.0) | John McGraw (86-62) | |
| 2 | 1898 | Baltimore Orioles | NL | 154 | 96 | 53 | 5 | .644 | 2nd of 12 | 933 | 623 | 27.1 | 25.4 | 24 | 7 | A.Maul (7.8) | Ned Hanlon (96-53) | |
| 3 | 1897 | Baltimore Orioles | NL | 136 | 90 | 40 | 6 | .692 | 2nd of 12 | 964 | 674 | 27.1 | 23.1 | 20 | 8 | H.Jennings (7.3) | Ned Hanlon (90-40) | |
| 4 | 1896 | Baltimore Orioles | NL | 132 | 90 | 39 | 3 | .698 | 1st of 12 | 995 | 662 | 26.8 | 25.7 | 22 | 9 | H.Jennings (8.3) | Ned Hanlon (90-39) | |
| 5 | 1895 | Baltimore Orioles | NL | 132 | 87 | 43 | 2 | .669 | 1st of 12 | 1009 | 646 | 25.4 | 25.9 | 20 | 8 | B.Hoffer (8.4) | Ned Hanlon (87-43) | |
| 6 | 1894 | Baltimore Orioles | NL | 129 | 89 | 39 | 1 | .695 | 1st of 12 | 1171 | 819 | 25.8 | 26.4 | 20 | 10 | J.Kelley (6.6) | Ned Hanlon (89-39) | |
| 7 | 1893 | Baltimore Orioles | NL | 130 | 60 | 70 | 0 | .462 | 8th of 12 | 820 | 893 | 26.2 | 26.7 | 25 | 8 | S.McMahon (5.6) | Ned Hanlon (60-70) | |
| 8 | 1892 | Baltimore Orioles | NL | 152 | 46 | 101 | 5 | .313 | 12th of 12 | 779 | 1020 | 28.0 | 25.6 | 37 | 14 | S.McMahon (3.4) | George Van Haltren (1-10), John Waltz (2-6) and Ned Hanlon (43-85) | |
| 9 | 1891 | Baltimore Orioles | AA | 139 | 71 | 64 | 4 | .526 | 4th of 9 | 850 | 798 | 26.6 | 23.7 | 18 | 6 | S.McMahon (9.1) | Billy Barnie (71-64) | |
| 10 | 1890 | Baltimore Orioles | AA | 38 | 15 | 19 | 4 | .441 | 6th of 9 | 182 | 192 | 25.0 | 21.8 | 18 | 5 | S.McMahon (2.1) | Billy Barnie (15-19) | |
| 11 | 1889 | Baltimore Orioles | AA | 139 | 70 | 65 | 4 | .519 | 5th of 8 | 791 | 795 | 26.6 | 24.0 | 23 | 5 | M.Kilroy (8.6) | Billy Barnie (70-65) | |
| 12 | 1888 | Baltimore Orioles | AA | 137 | 57 | 80 | 0 | .416 | 5th of 8 | 653 | 779 | 26.9 | 22.4 | 23 | 10 | T.Tucker (3.6) | Billy Barnie (57-80) | |
| 13 | 1887 | Baltimore Orioles | AA | 141 | 77 | 58 | 6 | .570 | 3rd of 8 | 975 | 861 | 25.7 | 21.3 | 17 | 9 | M.Kilroy (11.9) | Billy Barnie (77-58) | |
| 14 | 1886 | Baltimore Orioles | AA | 139 | 48 | 83 | 8 | .366 | 8th of 8 | 625 | 878 | 27.5 | 23.6 | 31 | 15 | M.Kilroy (5.9) | Billy Barnie (48-83) | |
| 15 | 1885 | Baltimore Orioles | AA | 110 | 41 | 68 | 1 | .376 | 8th of 8 | 541 | 683 | 25.5 | 22.6 | 32 | 11 | H.Henderson (7.6) | Billy Barnie (41-68) | |
| 16 | 1884 | Baltimore Orioles | AA | 108 | 63 | 43 | 2 | .594 | 6th of 13 | 636 | 515 | 26.7 | 23.1 | 19 | 5 | H.Henderson (6.6) | Billy Barnie (63-43) | |
| 17 | 1883 | Baltimore Orioles | AA | 96 | 28 | 68 | 0 | .292 | 8th of 8 | 471 | 742 | 25.7 | 22.2 | 29 | 8 | J.Clinton (2.1) | Billy Barnie (28-68) | |
| 18 | 1882 | Baltimore Orioles | AA | 74 | 19 | 54 | 1 | .260 | 6th of 6 | 272 | 513 | 25.5 | 26.5 | 23 | 8 | C.Householder (1.3) | Henry Myers (19-54) |