You can solve it with groupby.diff
Take the dataframe
df = pd.DataFrame({
'Day': [30, 30, 30, 30, 29, 29, 28, 28],
'Name': ['John', 'Mike', 'John', 'Mike', 'John', 'Mike', 'John', 'Mike'],
'Money': [100, 950, 200, 1000, 50, 50, 250, 1200],
'Expiry': [1, 1, 2, 2, 1, 1, 2, 2]
})
print(df)
Which looks like
Day Name Money Expiry
0 30 John 100 1
1 30 Mike 950 1
2 30 John 200 2
3 30 Mike 1000 2
4 29 John 50 1
5 29 Mike 50 1
6 28 John 250 2
7 28 Mike 1200 2
And the code
# make sure we have dates in the order we want
df.sort_values('Day', ascending=False)
# groubpy and get the difference from the next row in each group
# diff(1) calculates the difference from the previous row, so -1 will point to the next
df['Difference'] = df.groupby(['Name', 'Expiry']).Money.diff(-1)
Output
Day Name Money Expiry Difference
0 30 John 100 1 50.0
1 30 Mike 950 1 900.0
2 30 John 200 2 -50.0
3 30 Mike 1000 2 -200.0
4 29 John 50 1 NaN
5 29 Mike 50 1 NaN
6 28 John 250 2 NaN
7 28 Mike 1200 2 NaN