Raina, who did not play in the New Zealand ODI series after being named in the India squad due to an illness, played a captain's knock to help UP score 330 all out in their second innings at the SCA Stadium.
Raina hit nine fours and two sixes in his 106-ball innings. His innings is expected to draw attention of national selectors when they pick the Indian team for the home ODI series against England next month.
After Kuldeep was dismissed at the team score of 101, UP scored at 4.77 per over from that point with Raina leading from the front. His partnership of 140 with Chaudhary, who scored his maiden first-class century, helped swell the lead before they were bowled out for 330.
Chasing a stiff victory target of 377, Railways were reduced to 35 for 5 at stumps today as they suffered a top-order collapse.
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UP medium-pacer Praveen Kumar, playing his first match of the season, took wickets in consecutive overs to reduce Railways to 4 runs for 2 in the third over.
Railways could not quite recover from this as they went on the defensive, and crawled to 35 for 5 in 27 overs at the close of play today.
Only opener Shivakant Shukla (13) could reach double digit score out of the five Railways batsmen dismissed so far.
Railways now require another 342 runs for a win with five second innings wickets in hand.
Brief Scores:
Uttar Pradesh: 259 & 330 all out in 90 overs (Shivam Chaudhary 124, Suresh Raina 91; Karn Sharma 5/71).
Railways 213 & 35 for 5 in 27 overs.