This can happen in three cases:
if Daniil Medvedev doesn’t reach the final of the ATP-250 Los Cabos tournament next week;
if Medvedev does not reach the quarter-finals of the Montreal Masters;
if Medvedev does not reach the semi-finals in Los Cabos and the third round in Montreal.
These are the provisions, provided that Zverev himself does not play at the Canadian Masters.
However, Medvedev can retain the front row if Zverev takes part in the Montreal tournament. This will happen in four cases:
if Medvedev reaches the final in Los Cabos and achieves a similar result with Zverev in Montreal;
if Medvedev reaches the semi-finals in Los Cabos and goes one lap ahead of Zverev in Montreal;
if Medvedev reaches the quarter-finals in Montreal and Zverev loses in the second round;
if Medvedev goes one round further than Zverev in Montreal from the quarter-finals.
Source: Sport

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