Wilt Chamberlain has missed the most free throws in a season, with 578 misses in 1967-68.

most missed free throws in a single season
Interpreted as:
most missed free throws by a player in a single season
1967-68Chamberlain1961-62Chamberlain1960-61Chamberlain1966-67Chamberlain1963-64Chamberlain1968-69Chamberlain1965-66Chamberlain2000-01O'Neal1964-65Chamberlain1962-63Chamberlain1959-60Chamberlain2004-05O'Neal1994-95O'Neal1999-00O'Neal1993-94O'Neal2015-16Drummond2010-11Howard2007-08Howard2012-13Howard2015-16Jordan2008-09Howard2003-04O'Neal2009-10Howard1997-98O'Neal2001-02O'Neal578528523489476475475473472453414412399392379378370368366353345345333322319
NAMESEASONTMGPFT MISSMPGPPGRPGAPGSPGBPGTPGFGMFGAFG%3PM3PA3P%FTMFTAFT%MINPTSREBASTSTLBLKTOVPF+/-
Wilt ChamberlainWilt Chamberlain1967-68PHIPHI8257846.824.323.88.610.016.859.54.311.438.03,8361,9921,952702160
Wilt ChamberlainWilt Chamberlain1961-62PHIPHI8052848.550.425.72.420.039.550.610.417.061.33,8824,0292,052192123
Wilt ChamberlainWilt Chamberlain1960-61PHIPHI7952347.838.427.21.915.831.150.96.713.350.43,7733,0332,149148130
Wilt ChamberlainWilt Chamberlain1966-67PHIPHI8148945.524.124.27.89.714.268.34.810.844.13,6821,9561,957630143
Wilt ChamberlainWilt Chamberlain1963-64SFWSFW8047646.136.922.35.015.128.752.46.812.753.13,6892,9481,787403182
Wilt ChamberlainWilt Chamberlain1968-69LALLAL8147545.320.521.14.57.913.658.34.710.644.63,6691,6641,712366142
Wilt ChamberlainWilt Chamberlain1965-66PHIPHI7947547.333.524.65.213.625.254.06.312.451.33,7372,6491,943414171
Shaquille O'NealShaquille O'Neal2000-01LALLAL7447339.528.712.73.70.62.82.911.019.257.20.00.00.06.713.151.32,9242,12594027747204218256+463
Wilt ChamberlainWilt Chamberlain1964-65TOT7347245.234.722.93.414.628.551.05.612.146.43,3012,5341,673250146
Wilt ChamberlainWilt Chamberlain1962-63SFWSFW8045347.644.824.33.418.334.652.88.313.959.33,8063,5861,946275136
Wilt ChamberlainWilt Chamberlain1959-60PHIPHI7241446.437.627.02.314.832.146.18.013.858.23,3382,7071,941168150
Shaquille O'NealShaquille O'Neal2004-05MIAMIA7341234.122.910.42.70.52.32.89.015.060.10.00.04.810.546.12,4921,66976020036171203262+470
Shaquille O'NealShaquille O'Neal1994-95ORLORL7939937.029.311.42.70.92.42.611.820.258.30.00.10.05.810.853.32,9232,31590121473192204258
Shaquille O'NealShaquille O'Neal1999-00LALLAL7939240.029.713.63.80.53.02.812.121.157.40.00.00.05.510.452.43,1632,3441,07829936239223255+706
Shaquille O'NealShaquille O'Neal1993-94ORLORL8137939.829.313.22.40.92.92.711.819.659.90.00.00.05.810.555.43,2242,3771,07219576231222281
Andre DrummondAndre Drummond2015-16DETDET8137832.916.214.80.81.51.41.96.813.152.10.00.133.32.67.235.52,6651,3141,19867119112155245+126
Dwight HowardDwight Howard2010-11ORLORL7837037.622.914.11.41.42.43.67.913.459.30.00.10.07.011.759.62,9351,7841,098107107186279258+498
Dwight HowardDwight Howard2007-08ORLORL8236837.720.714.21.30.92.13.27.111.959.90.00.00.06.510.959.03,0881,6951,16111074176263274+484
Dwight HowardDwight Howard2012-13LALLAL7636635.817.112.41.41.12.43.06.210.757.80.00.116.74.79.549.22,7221,29694510884186225291+140
DeAndre JordanDeAndre Jordan2015-16LACLAC7735333.712.713.81.20.72.31.44.66.670.30.00.00.03.58.043.02,5989801,0599051177107207+440
Dwight HowardDwight Howard2008-09ORLORL7934535.720.613.81.41.02.93.07.112.457.20.00.00.06.410.759.42,8211,6241,09311277231240270+553
Shaquille O'NealShaquille O'Neal2003-04LALLAL6734536.821.511.52.90.52.52.98.314.158.40.00.04.910.149.02,4641,43976919634166195225+437
Dwight HowardDwight Howard2009-10ORLORL8233334.718.313.21.80.92.83.36.210.261.20.00.10.05.910.059.22,8431,5031,08214475228274287+619
Shaquille O'NealShaquille O'Neal1997-98LALLAL6032236.328.311.42.40.72.42.911.219.158.40.00.06.011.452.72,1751,69968114239144175193+649
Shaquille O'NealShaquille O'Neal2001-02LALLAL6731936.127.210.73.00.62.02.610.618.357.90.00.00.05.910.755.52,4221,82271520041137171199+566