Resuming at 59 for no loss, the Mohammad Kaif-led side surpassed TNCA President's total of 207 in 78.5 overs, with just five wickets down.
Opener Gupta smashed eight fours and four sixes in his 243-ball knock to see his side through.
Gupta shared a valuable fifth-wicket partnership of 104 runs with Akshdeep Nath (47).
For TNCA President XI, left-arm spinner R Aushik Srinivas took four for 51 while off-spinner M Sharukh Khan claimed a wicket.
