Only a late Darren Pratley goal had stopped Eastleigh from progressing to the fourth round at the first time of asking, and the Trotters midfielder also played a crucial part in the replay.
Emirates FA Cup
Third round replays
Tuesday 19 January 2016
Winning sides receive £67,500 from The FA prize fund
The Bolton captain fired home just before the hour mark as Championship side Bolton, who play three leagues above Eastleigh, won 3-2 to book a fourth round game at home to Leeds United.
Joe Partington’s superb finish had put the Spitfires ahead 11 minutes in, but quickfire strikes from Gary Madine and Dean Moxey looked to have swung the match in Bolton’s favour.
A cool effort from Kaid Mohamed then restored parity for Eastleigh on the stroke of half-time – only for Pratley to have the last word.
But League Two Portsmouth defied the divisional gap and can now look forward to a south-coast tie against Bournemouth after first-half goals from Gary Roberts and Marc McNulty were enough to beat Ipswich Town.
Roberts dusted himself off after being fouled by Piotr Malarczyk to open the scoring with a penalty and moments later, an unmarked McNulty nodded in.
England Under-19s star Ainsley Maitland-Niles pulled one back for Ipswich, but the Championship outfit were second best and succumbed to a 2-1 defeat.
It sets up an intriguing clash between Pompey and Bournemouth who, having beaten Chelsea and Manchester United in their first season in the Premier League, are no strangers to upsets themselves.
Third round replay night also involved the drama of penalties and defender Mark Ellis was the hero for Carlisle United as they beat Yeovil Town 5-4 on penalties.
Antony Sweeney levelled for Carlisle in the second half after Jack Compton had put Yeovil ahead, but both sides finished extra time a man down after red cards to Alex Lacey and Luke Joyce.
But Matthew Dolan’s penalty miss handed Ellis the opportunity to win it for Carlisle, who now entertain Everton.
Bury downed last year’s quarter-finalists Bradford City, as Jacob Mellis clinched a 4-2 penalty shootout win after a stalemate over 20 minutes. Bury play Hull City next.
Premier League Aston Villa left it late to beat Wycombe Wanderers but now face Manchester City at Villa Park after Ciaran Clark and Idrissa Gueye secured a 2-0 victory.
League Two’s Wycombe had held the Villans 1-1 in the initial clash and had their chances this time around, Garry Thompson going close with two headers.
But Villa grew into the game and turned the screw in the 75th minute when Clark connected with an Ashley Westwood cross, before substitute Gueye wrapped up the game.
Matej Vydra was the star on parade for Reading as his hat-trick inspired a 5-2 victory over 10-man Huddersfield – who had initally taken a two-goal lead.
Jonathan Hogg was sent off for after pulling down Vydra as the last man after Jamie Paterson and Tommy Smith had opened the scoring for the Terriers.
Lucas Piazon scored from the resulting free-kick, and Vydra collected his goals in the first half before Alex Fernandez’s long-range strike confirmed a next round tie against Walsall.
MK Dons meanwhile set up a glamour clash against Chelsea after second-half penalties from Ben Reeves and Simon Church, either side of Josh Murphy’s strike, sealed a 3-0 victory over Northampton Town.
And at Ashton Gate, Salomon Rondon’s first Emirates FA Cup goal proved enough for West Bromwich Albion against Bristol City, with the Baggies now in line to face Peterborough.
Emirates FA Cup highlights: Bolton Wanderers 3-2 Eastleigh