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Stockholders' Deficit
 3 Months Ended
Apr. 30, 2020
Equity [Abstract]  
Stockholders' Deficit Stockholders' Deficit

Changes in stockholders' deficit by component, net of tax, for the three months ended April 30, 2020, are as follows:
(in millions, except per share data)
Common stock and additional paid-in capital
 
Accumulated other comprehensive loss
 
Accumulated deficit
 
Total stockholders' deficit
Shares
 
Amount
 
Balances, January 31, 2020
219.4

 
$
2,317.0

 
$
(160.3
)
 
$
(2,295.8
)
 
$
(139.1
)
Common shares issued under stock plans
1.0

 
24.3

 
—

 
—

 
24.3

Stock-based compensation expense
—

 
88.2

 
—

 
—

 
88.2

Settlement of liability-classified restricted stock units
—

 
28.7

 
—

 
—

 
28.7

Post-combination expense related to equity awards assumed
—

 
0.1

 
—

 
—

 
0.1

Net income
—

 
—

 
—

 
66.5

 
66.5

Other comprehensive loss
—

 
—

 
(18.8
)
 
—

 
(18.8
)
Repurchase and retirement of common shares
(1.2
)
 
(57.0
)
 
—

 
(132.0
)
 
(189.0
)
Balances, April 30, 2020
219.2

 
2,401.3

 
(179.1
)
 
(2,361.3
)
 
(139.1
)
 ________________
(1)
During the three months ended April 30, 2020, Autodesk repurchased 1.2 million shares at an average repurchase price of $153.41 per share. At April 30, 2020, 13.5 million shares remained available for repurchase under the repurchase program approved by the Board of Directors.

Changes in stockholders' deficit by component, net of tax, for the three months ended April 30, 2019, are as follows:
 
Common stock and additional paid-in capital
 
Accumulated other comprehensive loss
 
Accumulated deficit
 
Total stockholders' deficit
Shares
 
Amount
 
Balances, January 31, 2019
219.4

 
$
2,071.5

 
$
(135.0
)
 
$
(2,147.4
)
 
$
(210.9
)
Common shares issued under stock plans
0.8

 
21.1

 
—

 
—

 
21.1

Stock-based compensation expense
—

 
75.2

 
—

 
—

 
75.2

Post combination expense related to assumed equity
—

 
0.8

 
—

 
—

 
0.8

Cumulative effect of accounting changes
—

 
—

 
—

 
(0.7
)
 
(0.7
)
Net loss
—

 
—

 
—

 
(24.2
)
 
(24.2
)
Other comprehensive loss
—

 
—

 
(6.6
)
 
—

 
(6.6
)
Repurchase and retirement of common shares
(0.6
)
 
(45.5
)
 
—

 
(54.5
)
 
(100.0
)
Balances, April 30, 2019
219.6

 
2,123.1

 
(141.6
)
 
(2,226.8
)
 
(245.3
)