Hopes Chester FC could mount an FA Trophy were ended on a disappointing night at the Swansway Chester Stadium.
AFC Telford United progressed to the second round on penalties after the first round replay finished 1-1 at the end of extra time.
Ben Heneghan gave the Blues the lead after 15 minutes and Telford, who are bottom of the Vanarama Conference, did not manage a shot on target until the 67th minute.
Chester had looked well on top in the first half but tailed off after the break and the Bucks equalised through Sam Smith with 14 minutes to go.
Extra time came and went with half chances for both teams but the game had become ragged as fatigue kicked in and went to penalties.
Telford keeper Jonathan Hedge made excellent saves to his left from Kingsley James and Tom Peers and the Shropshire side went through 4-3 despite Smith blasting his spot kick over the bar.
Chester have now gone five games without a win in all competitions and must dust themselves down for three important festive league fixtures.
Tell us what YOU made of the team's display by rating each player from one to 10.
We'll publish the results in this week's Chester Chronicle.
