Johannesburg - Wits lost 4-3 on penalties to Free State Stars in their Telkom Knockout quarter-final match at Bidvest Stadium on Saturday.
Two missed penalties, one by Papy Faty and one from Terror Fanteni saw the Clever Boys miss out on a semi-final spot in the competition.
Luyolo Nomandela scored, with the fifth penalty for visitors, the winning penalty to edge the Students after a tight encounter.
After the scores remained goalless after regulation time, 30 minutes of extra time were played but neither side could make the breakthrough.
Both sides on the night played tentatively and were cautious in their approach and few opportunities were created as a result.
In a dull first period, devoid of clear-cut chances, neither side was able to dominate the game.
Four minutes into the encounter Katlego Mashego for the visitors, started off the match with a horrible miscue. He completely missed the ball with a regulation clearance in the box. Mzikayise Mashaba was able to gather the ball and ran to the touchline but his shot was nowhere near the target.
In the opening 25 minutes, Mashaba made a number of good runs down the left, but he could not get the cross into the area, or receive support.
Just after the half hour mark, Mashego went on a bustling run down the middle of the field. On the edge of the area - still in space - he nudged the ball too far ahead and the Wits defence were able to snuffle out the menacing attack.
On the cusp of half-time, Moeketsi Mvula was the closest to scoring for the visitors. He rose to meet a cross in the Wits area, but his well-struck header went just over the crossbar.
In the 50th minute Mashego sprinted down the centre from a fast Stars counter-attack, and his scorching strike from outside the box clattered into the crossbar to deny his side the lead.
Mashego was again thwarted by the woodwork in the 87th minute. From a ball given away by Wits near the halfway line, Mashego gathered and unleashed a thunderbolt shot from way out, which caught Ryan Harrison in-goal completely off guard. The crossbar, however, came to the rescue and the score remained goalless and stayed that way heading into extra-time.
In the second period of extra-time, Mashego spurned the easiest chance of the match. Calvin Kadi made a breathtaking run down the left, and delivered the ball in the perfect position in the box for his team-mate. Mashego, however, managed to miss from close range with an open goal glaring wide at the Wits player.