Monty and Harrington downed the Spanish duo of Ignacio Garrido and Miguel Angel Jimenez. Ian Poulter won his third consecutive match, as he partnered with Justin Rose to down Sergio Garcia and Thomas Bjorn, 2-and-1.
The Continental European squad picked up two victories as well in the afternoon foursomes matches. Fredrik Jacobson and Niclas Fasth teamed to hand Paul Lawrie and Paul Casey a 3-and-2 loss. Alex Cejka and Raphael Jacquelin rolled to their fourth win in four matches as they pounded David Howell and Lee Westwood, 5-and-3.
The Continental European team had earned a 2 1/2 - 1 1/2 win in the morning greensomes matches to narrow the gap.
'It was a very tough day out there,' said Montgomerie. 'I think we got out of jail a little bit this morning ending the session only one point behind when it could easily have been two and then this afternoon we ended all square.'
Ballesteros, who took the afternoon match off, knows his team will be in for a tough fight on Sunday.
'It is a bit better than last year (when Continental Europe trailed by four points going into the singles), but it is still a big margin to make up and it is going to be a tough day,' Ballesteros said.
In the opening match of the afternoon, Monty and Harrington fell 1-down when they bogeyed the first hole. However, the pair rallied to square the match with a birdie on the par-5 third.
Garrido and Jimenez converted a birdie at the sixth to retake a 1-up lead. Monty and Harrington fought right back with a birdie at the next to even the match again.
Montgomerie, who teamed with Justin Rose to earn a 1/2-point despite trailing 3-down with three holes to go in the morning, rallied with Harrington on the back nine. The duo won the 10th and 12th with birdies to grab a 2-up lead.
The Spaniards rallied with back-to-back wins from the 14th to square the match. Monty rolled in an eight-footer for birdie on the 16th to gain a 1-up lead. Garrido then missed a par save on 17 and conceded the birdie try to Harrington giving the Irishman and Monty a 2-and-1 win.
Jacobson and Fasth took control early in their match and played steady golf throughout. The duo birdied the first for an early lead, but the match was squared when Lawrie and Casey carded an eagle on the fifth.
The Swedish duo came right back to win No. 6. The teams then halved the following six holes around the turn but Jacobson and Fasth extended their lead to 2-up with a birdie at the 13th. Another birdie on 15 stretched the cushion to 3-up and the match was their's after the teams halved the 16th.
The dynamic pairing of Cejka and Jacquelin birdied three of the first four holes against Howell and Westwood for a quick 3-up advantage. The Englishmen cut it to 2-down with a birdie on the eighth.
Around the turn, Cejka and Jacquelin won back-to-back holes from the 10th to take a 4-up lead. The English duo parred the 12th to get back within 3-down but Cejka ran home a lengthy birdie putt on the 14th to push the lead back to 4-up with four holes to go.
On the 15th, Westwood pulled his second shot left behind some trees while Cejka knocked his second over the green. Jacquelin's chip came to rest within a few feet of the cup, while Howell and Westwood were unable to get up-and- down. They conceded the birdie and the 5-and-3 win to Cejka and Jacquelin.
Former Ryder Cup duo Garcia and Bjorn managed to par the first hole, which gave them a 1-up lead. The English duo of Rose and Poulter came right back to square the match at the second with a par of their own. Garcia and Bjorn birdied the sixth to regain their 1-up lead.
The Englishmen however birdied Nos. 7 and 8 to grab a 1-up lead of their own. They moved it to 2-up with a birdie at the 10th but Garcia and Bjorn responded with a win in No. 11 to get back within 1-down.
On No. 15, Rose dropped his duo's third shot within 10 feet from 95 yards out, while Garcia's approach came to rest some 18 feet from the cup. After Bjorn missed his birdie try, Poulter ran in his birdie putt for the 2-and-1 victory.
'We had a ding-dong game out there and when we looked at the scoreboard coming down the final few holes, we realized how important it was to the overall position for us to get the point and we were delighted to do so,' said Rose.
The teams will face off in the traditional 10 singles matches on Sunday. Great Britain and Ireland, the defending champions, need to earn 4 1/2 points Sunday to retain the trophy. Monty thinks his team is prepared to conquer their foes.
'We need 4 1/2 points and the mood in our team room is as it has been all week, very upbeat and we are looking forward to the challenge,' Monty said.