Jon Lester had a 77-44 record with an ERA of 3.64 and 940 strikeouts in 171 appearances for the Cubs in his career.
| NAME | SEASON | TM | G | W | L | W% | GS | ERA | SO | CG | SHO | SV | IP | H | ER | R | HR | BB | HBP | GF | IBB | TBF | WP | K/9 | BB/9 | K/BB | HR/9 | K% | BB% | WHIP | BABIP | RA | ERA- | FIP | FIP- | H/9 | PRAA | ||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 |  | J. Lester | 2015 |  CHC | 32 | 11 | 12 | .478 | 32 | 3.34 | 207 | 1 | 0 | 0 | 205.0 | 183 | 76 | 83 | 16 | 47 | 7 | 0 | 0 | 828 | 8 | 9.09 | 2.06 | 4.40 | 0.70 | 25.0 | 5.7 | 1.12 | .303 | 3.64 | 85 | 2.91 | 75 | 8.03 | 21.9 |
| 2 | | J. Lester | 2016 | CHC | 32 | 19 | 5 | .792 | 32 | 2.44 | 197 | 2 | 0 | 0 | 202.2 | 154 | 55 | 57 | 21 | 52 | 6 | 0 | 0 | 796 | 4 | 8.75 | 2.31 | 3.79 | 0.93 | 24.7 | 6.5 | 1.02 | .256 | 2.53 | 59 | 3.40 | 82 | 6.84 | 16.3 |
| 3 | | J. Lester | 2017 | CHC | 32 | 13 | 8 | .619 | 32 | 4.33 | 180 | 1 | 0 | 0 | 180.2 | 179 | 87 | 101 | 26 | 60 | 4 | 0 | 3 | 763 | 3 | 8.97 | 2.99 | 3.00 | 1.30 | 23.6 | 7.9 | 1.32 | .310 | 5.03 | 100 | 4.09 | 95 | 8.92 | 4.5 |
| 4 | | J. Lester | 2018 | CHC | 32 | 18 | 6 | .750 | 32 | 3.32 | 149 | 0 | 0 | 0 | 181.2 | 174 | 67 | 75 | 24 | 64 | 6 | 0 | 1 | 761 | 4 | 7.38 | 3.17 | 2.33 | 1.19 | 19.6 | 8.4 | 1.31 | .290 | 3.72 | 83 | 4.39 | 109 | 8.62 | -7.6 |
| 5 | | J. Lester | 2019 | CHC | 31 | 13 | 10 | .565 | 31 | 4.46 | 165 | 0 | 0 | 0 | 171.2 | 205 | 85 | 101 | 26 | 52 | 5 | 0 | 0 | 764 | 3 | 8.65 | 2.73 | 3.17 | 1.36 | 21.6 | 6.8 | 1.50 | .347 | 5.30 | 101 | 4.25 | 96 | 10.75 | 3.4 |
| 6 | | J. Lester | 2020 | CHC | 12 | 3 | 3 | .500 | 12 | 5.16 | 42 | 0 | 0 | 0 | 61.0 | 64 | 35 | 35 | 11 | 17 | 3 | 0 | 0 | 265 | 2 | 6.20 | 2.51 | 2.47 | 1.62 | 15.8 | 6.4 | 1.33 | .276 | 5.16 | 117 | 5.13 | 117 | 9.44 | -5 |
| Total | 171 | 77 | 44 | .636 | 171 | 3.64 | 940 | 4 | 0 | 0 | 1002.2 | 959 | 405 | 452 | 124 | 292 | 31 | 0 | 4 | 4,177 | 24 | 8.44 | 2.62 | 3.22 | 1.11 | 22.5 | 7.0 | 1.25 | .299 | 4.06 | 87 | 3.85 | 92 | 8.61 | 33.5 |
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