Khris Middleton vs. Charles Oakley Season by Season Comparison

Side by side comparison of each NBA season of Charles Oakley and Khris Middleton, from their rookie seasons to their last year played, in chronological order with awards, stats, championships and playoff performance of their teams every year.

Player comparisons:
Career comparison / Season by season

Who had the better rookie season? Who had best stats in their 10th season? Who won a championship first? These questions and many others, are answered here.

Khris Middleton played 12 years in the NBA, 7 less than Charles Oakley, who played 19. Khris Middleton had the first of his seasons in 2012-13, while Charles Oakley had his rookie season in 1985-86. With that starting point, here you can take a look at each of their seasons side by side and compare how their careers evolved in achivements, awards and championships won, the stats they recorded both in the Regular Season and the Playoffs and how their teams performed in the postseason.

Their Careers

Player
Total Seasons Playoffs Played NBA Years
Khris Middleton 12 9 2012-13 to 2023-24
Charles Oakley 19 15 1985-86 to 2003-04

Comparison Season by Season

Jump to season:
1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19

Rookie Season

Khris Middleton Charles Oakley
Season 2012-131985-86
Team Detroit PistonsChicago Bulls
Honors & Awards -Achievement All-Rookie First Team
Playoffs Did Not PlayBulls Lost East Conf 1st Rd
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 27 17.6 6.1 0.1 1.7 1.9 1.0 0.6 0.1 0.4 2.0 2.3 5.2 .440 0.5 1.7 .311 1.0 1.2 .844
Charles Oakley 77 23.0 9.6 3.3 5.3 8.6 1.7 0.9 0.4 2.3 3.2 3.6 7.0 .519 0.0 0.0 .000 2.3 3.5 .662
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley 3 29.3 10.0 3.3 6.7 10.0 1.0 2.0 0.7 1.7 4.3 3.7 7.0 .524 0.0 0.0 - 2.7 4.3 .615

Season 2

Khris Middleton Charles Oakley
Season 2013-141986-87
Team Milwaukee BucksChicago Bulls
Honors & Awards
Playoffs Did Not PlayBulls Lost East Conf 1st Rd
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 82 30.0 12.1 0.7 3.0 3.8 2.1 1.0 0.2 1.5 3.0 4.6 10.4 .440 1.5 3.5 .414 1.4 1.7 .861
Charles Oakley 82 36.3 14.5 3.6 9.5 13.1 3.6 1.0 0.4 3.6 3.8 5.7 12.8 .445 0.1 0.4 .367 3.0 4.4 .686
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley 3 43.0 20.0 5.7 9.7 15.3 2.0 1.3 0.3 2.7 4.3 6.3 16.7 .380 0.7 1.3 .500 6.7 8.0 .833

Season 3

Khris Middleton Charles Oakley
Season 2014-151987-88
Team Milwaukee BucksChicago Bulls
Honors & Awards
Playoffs Bucks Lost East Conf 1st RdBulls Lost East Conf Semis
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 79 30.1 13.4 0.6 3.8 4.4 2.3 1.5 0.1 1.4 2.3 5.1 11.0 .467 1.4 3.4 .407 1.7 2.0 .859
Charles Oakley 82 34.3 12.4 4.0 9.0 13.0 3.0 0.8 0.3 2.9 3.3 4.6 9.5 .483 0.0 0.1 .250 3.2 4.4 .727
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 6 38.7 15.8 1.2 2.5 3.7 2.0 2.3 0.5 1.7 2.3 5.8 15.3 .380 1.8 5.7 .324 2.3 2.5 .933
Charles Oakley 10 37.3 10.1 3.9 8.9 12.8 3.2 0.6 0.4 1.8 3.3 4.0 9.1 .440 0.0 0.2 .000 2.1 2.4 .875

Season 4

Khris Middleton Charles Oakley
Season 2015-161988-89
Team Milwaukee BucksNew York Knicks
Honors & Awards
Playoffs Did Not PlayKnicks Lost East Conf Semis
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 79 36.1 18.2 0.6 3.3 3.8 4.2 1.7 0.2 2.3 2.6 6.4 14.5 .444 1.8 4.6 .396 3.5 3.9 .888
Charles Oakley 82 31.8 12.9 4.2 6.3 10.5 2.3 1.3 0.2 3.0 3.3 5.2 10.2 .510 0.1 0.6 .250 2.4 3.1 .773
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley 9 33.2 9.7 4.8 6.4 11.2 1.2 1.3 0.1 2.4 3.4 3.9 8.1 .479 0.1 0.2 .500 1.8 2.7 .667

Season 5

Khris Middleton Charles Oakley
Season 2016-171989-90
Team Milwaukee BucksNew York Knicks
Honors & Awards
Playoffs Bucks Lost East Conf 1st RdKnicks Lost East Conf Semis
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 29 30.7 14.7 0.4 3.9 4.2 3.4 1.4 0.2 2.2 2.7 5.2 11.5 .450 1.6 3.6 .433 2.8 3.2 .880
Charles Oakley 61 36.0 14.6 4.2 7.7 11.9 2.4 1.0 0.3 2.7 3.6 5.5 10.5 .524 0.0 0.0 .000 3.6 4.7 .761
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 6 38.5 14.5 0.0 4.7 4.7 5.3 2.0 0.0 1.8 2.8 5.2 13.0 .397 1.2 3.2 .368 3.0 3.7 .818
Charles Oakley 10 33.6 12.1 3.9 7.1 11.0 2.7 1.1 0.2 2.2 3.3 4.3 8.4 .512 0.1 0.1 1.000 3.4 5.2 .654

Season 6

Khris Middleton Charles Oakley
Season 2017-181990-91
Team Milwaukee BucksNew York Knicks
Honors & Awards
Playoffs Bucks Lost East Conf 1st RdKnicks Lost East Conf 1st Rd
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 82 36.4 20.1 0.5 4.7 5.2 4.0 1.5 0.3 2.3 3.3 7.2 15.5 .466 1.8 5.0 .359 3.9 4.4 .884
Charles Oakley 76 36.0 11.2 4.0 8.1 12.1 2.7 0.8 0.2 2.8 3.8 4.0 7.8 .516 0.0 0.0 .000 3.1 4.0 .784
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 7 39.3 24.7 0.1 5.0 5.1 3.1 0.9 0.7 2.3 4.3 9.6 16.0 .598 3.6 5.9 .610 2.0 2.7 .737
Charles Oakley 3 33.3 7.7 5.0 5.3 10.3 1.0 0.7 0.3 2.3 4.3 3.3 7.0 .476 0.0 0.0 - 1.0 2.0 .500

Season 7

Khris Middleton Charles Oakley
Season 2018-191991-92
Team Milwaukee BucksNew York Knicks
Honors & Awards Achievement All-Star Game-
Playoffs Bucks Lost East Conf FinalsKnicks Lost East Conf Semis
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 77 31.1 18.3 0.6 5.3 6.0 4.3 1.0 0.1 2.3 2.2 6.6 14.9 .441 2.3 6.2 .378 2.8 3.4 .837
Charles Oakley 82 28.2 6.2 3.1 5.4 8.5 1.6 0.8 0.2 1.5 3.1 2.6 4.9 .522 0.0 0.0 .000 1.0 1.4 .735
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 15 34.3 16.9 0.6 5.7 6.3 4.4 0.6 0.0 1.9 2.9 5.6 13.4 .418 2.7 6.1 .435 3.1 3.5 .885
Charles Oakley 12 29.5 5.3 3.7 5.3 9.0 0.7 0.7 0.4 1.3 3.0 1.8 4.8 .379 0.0 0.0 - 1.7 2.3 .741

Season 8

Khris Middleton Charles Oakley
Season 2019-201992-93
Team Milwaukee BucksNew York Knicks
Honors & Awards Achievement All-Star Game-
Playoffs Bucks Lost East Conf SemisKnicks Lost East Conf Finals
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 62 29.9 20.9 0.7 5.5 6.2 4.3 0.9 0.1 2.2 2.3 7.6 15.3 .497 2.4 5.7 .415 3.4 3.7 .916
Charles Oakley 82 27.2 6.9 3.5 5.1 8.6 1.5 1.0 0.2 1.5 3.5 2.7 5.3 .508 0.0 0.0 .000 1.5 2.1 .722
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 10 35.5 20.3 0.5 6.4 6.9 6.0 1.1 0.2 3.4 4.1 7.1 18.0 .394 2.3 6.5 .354 3.8 4.6 .826
Charles Oakley 15 33.8 11.1 4.7 6.3 11.0 1.1 1.1 0.1 2.4 3.4 4.2 8.7 .481 0.0 0.0 - 2.7 3.7 .727

Season 9

Khris Middleton Charles Oakley
Season 2020-211993-94
Team Milwaukee BucksNew York Knicks
Honors & Awards -Achievement All-Defensive First Team
-Achievement All-Star Game
Playoffs NBA Champion NBA ChampionKnicks Lost NBA Finals
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 68 33.4 20.4 0.8 5.2 6.0 5.4 1.1 0.1 2.6 2.4 7.5 15.8 .476 2.2 5.4 .414 3.1 3.5 .898
Charles Oakley 82 35.8 11.8 4.3 7.5 11.8 2.7 1.3 0.2 2.4 3.6 4.4 9.3 .478 0.0 0.0 .000 3.0 3.8 .776
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 23 40.1 23.6 1.1 6.5 7.6 5.1 1.5 0.2 3.2 2.5 8.6 19.7 .438 2.6 7.6 .343 3.7 4.2 .887
Charles Oakley 25 39.7 13.2 4.6 7.0 11.7 2.4 1.4 0.2 2.6 3.5 5.0 10.5 .477 0.0 0.0 - 3.2 4.1 .775

Season 10

Khris Middleton Charles Oakley
Season 2021-221994-95
Team Milwaukee BucksNew York Knicks
Honors & Awards Achievement All-Star Game-
Playoffs Bucks Lost East Conf SemisKnicks Lost East Conf Semis
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 66 32.4 20.1 0.6 4.8 5.4 5.4 1.2 0.3 2.9 2.4 6.8 15.5 .443 2.5 6.6 .373 3.9 4.4 .890
Charles Oakley 50 31.3 10.1 3.1 5.8 8.9 2.5 1.2 0.1 2.1 3.6 3.8 7.9 .489 0.1 0.2 .250 2.4 3.0 .793
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 2 36.0 14.5 0.5 4.5 5.0 7.0 1.5 0.0 5.5 3.0 5.0 12.0 .417 3.0 7.0 .429 1.5 1.5 1.000
Charles Oakley 11 38.3 13.1 2.8 5.6 8.5 3.7 1.7 0.5 2.2 3.8 4.5 9.9 .450 0.4 0.9 .400 3.8 4.6 .824

Season 11

Khris Middleton Charles Oakley
Season 2022-231995-96
Team Milwaukee BucksNew York Knicks
Honors & Awards
Playoffs Bucks Lost East Conf 1st RdKnicks Lost East Conf Semis
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 33 24.3 15.1 0.8 3.4 4.2 4.9 0.7 0.2 2.2 2.1 5.4 12.3 .436 1.5 4.9 .315 2.8 3.1 .902
Charles Oakley 53 33.5 11.4 3.1 5.6 8.7 2.6 1.1 0.3 2.0 3.7 4.0 8.5 .471 0.1 0.5 .269 3.3 4.0 .833
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 5 34.6 23.8 1.4 5.0 6.4 6.2 0.6 0.0 3.4 3.0 8.0 17.2 .465 2.6 6.4 .406 5.2 6.0 .867
Charles Oakley 8 38.5 13.1 3.5 5.1 8.6 1.8 1.0 0.0 3.5 4.1 4.9 9.8 .500 0.3 0.8 .333 3.1 4.5 .694

Season 12

Khris Middleton Charles Oakley
Season 2023-241996-97
Team Milwaukee BucksNew York Knicks
Honors & Awards
Playoffs Bucks Lost East Conf 1st RdKnicks Lost East Conf Semis
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 55 27.0 15.1 0.7 3.9 4.7 5.3 0.9 0.3 2.3 2.6 5.8 11.7 .493 1.7 4.5 .381 1.8 2.2 .833
Charles Oakley 80 35.9 10.8 3.1 6.7 9.8 2.8 1.4 0.3 2.1 3.8 4.2 8.7 .488 0.1 0.2 .263 2.3 2.8 .808
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton 6 38.3 24.7 2.0 7.2 9.2 4.7 0.5 0.2 2.3 4.2 9.2 19.0 .482 1.8 5.2 .355 4.5 5.0 .900
Charles Oakley 10 35.8 9.8 2.3 6.5 8.8 1.6 2.2 0.3 1.8 3.7 3.8 8.6 .442 0.0 0.1 .000 2.2 2.9 .759

Season 13

Khris Middleton Charles Oakley
Season -1997-98
Team -New York Knicks
Honors & Awards -Achievement All-Defensive Second Team
Playoffs -Knicks Lost East Conf Semis
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley 79 34.6 9.0 2.8 6.4 9.2 2.5 1.6 0.3 1.6 3.5 3.9 8.8 .440 0.0 0.1 .000 1.2 1.4 .851
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley 10 34.0 8.1 2.1 6.4 8.5 1.4 1.1 0.2 1.3 3.8 2.9 7.1 .408 0.0 0.0 - 2.3 2.5 .920

Season 14

Khris Middleton Charles Oakley
Season -1998-99
Team -Toronto Raptors
Honors & Awards
Playoffs -Did Not Play
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley 50 32.7 7.0 1.9 5.6 7.5 3.4 0.9 0.4 1.9 3.6 2.8 6.5 .428 0.0 0.1 .200 1.3 1.7 .807
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley ------- --- ----------

Season 15

Khris Middleton Charles Oakley
Season -1999-00
Team -Toronto Raptors
Honors & Awards
Playoffs -Raptors Lost East Conf 1st Rd
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley 80 30.4 6.9 1.5 5.3 6.8 3.2 1.3 0.6 1.9 3.7 2.9 7.0 .418 0.2 0.5 .341 0.8 1.1 .776
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley 3 37.0 10.0 0.7 7.0 7.7 3.7 2.0 0.3 1.7 4.7 4.7 9.7 .483 0.7 2.3 .286 0.0 0.3 .000

Season 16

Khris Middleton Charles Oakley
Season -2000-01
Team -Toronto Raptors
Honors & Awards
Playoffs -Raptors Lost East Conf Semis
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley 78 35.5 9.6 1.8 7.7 9.5 3.4 1.0 0.6 1.8 3.3 3.9 10.1 .388 0.1 0.6 .224 1.6 1.9 .836
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley 12 32.6 9.3 1.7 4.7 6.3 1.8 1.0 0.6 1.8 2.4 3.9 9.0 .435 0.3 0.7 .375 1.2 1.4 .824

Season 17

Khris Middleton Charles Oakley
Season -2001-02
Team -Chicago Bulls
Honors & Awards
Playoffs -Did Not Play
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley 57 24.3 3.8 1.3 4.8 6.0 2.0 0.9 0.2 1.5 3.1 1.7 4.6 .369 0.0 0.1 .167 0.4 0.5 .750
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley ------- --- ----------

Season 18

Khris Middleton Charles Oakley
Season -2002-03
Team -Washington Wizards
Honors & Awards
Playoffs -Did Not Play
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley 42 12.2 1.8 0.9 1.7 2.5 1.0 0.3 0.1 0.5 2.1 0.5 1.3 .418 0.0 0.0 - 0.7 0.8 .824
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley ------- --- ----------

Season 19

Khris Middleton Charles Oakley
Season -2003-04
Team -Houston Rockets
Honors & Awards
Playoffs -Did Not Play
more >>
Regular Season Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley 7 3.6 1.3 0.0 0.7 0.7 0.3 0.0 0.0 0.1 1.1 0.3 0.9 .333 0.0 0.0 - 0.7 0.9 .833
Playoffs Stats
G Min Pts ORb DRb Reb Ast Stl Blk TO PF FGM / A % 3PM / A % FTM / A %
Khris Middleton ------- --- ----------
Charles Oakley ------- --- ----------